2-溴-1,3-二乙基苯

反应条件: temp:-75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,6-Diethyl bromobenzene (38.2 g, 180.2 mmol) is added dropwise through an additional funnel over a 1 hour period to a solution of n-BuLi (2.0 M in cyclohexane, 99.1 mL, 198.2 mmol) in THF (380 mL) at −75° C. After addition, the reaction mixture is stirred at −75° C. for 30 minutes; trimethyl borate (28.1 g, 270.3 mmol) is added slowly over a 40 minute period. The reaction mixture is warmed to room temperature overnight. 2N HCl (250 mL) is added slowly and the resulting mixture is stirred for 1 hour. The organic layer is separated and the aqueous layer is extracted with ether (2×200 mL). The combined organic layers are dried over anhydrous Na2SO4 and the solvents are removed in vacuo. Hexane (400 mL) is added to the residue and a white precipitate is formed. Filtration and drying in vacuo give 2,6-diethylphenyl boronic acid as a white solid. 1H NMR: (CDCl3) 7.22 (t, 1H), 7.04 (s, 2H), 4.65 (s, 2H), 2.64 (q, 4H), 1.22 (t, 6H). After addition The reaction mixture is warmed to room temperature overnight the resulting mixture is stirred for 1 hour The organic layer is separated the aqueous layer is extracted with ether (2×200 mL) The combined organic layers are dried over anhydrous Na2SO4 the solvents are removed in vacuo Hexane (400 mL) is added to the residue a white precipitate is formed Filtration drying in vacuo

反应条件: temp:-75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,6-Diethyl bromobenzene (38.2 g, 180.2 mmol) is added dropwise through an additional funnel over a 1 hour period to a solution of n-BuLi (2.0 M in cyclohexane, 99.1 mL, 198.2 mmol) in THF (380 mL) at −75° C. After addition, the reaction mixture is stirred at −75° C. for 30 minutes; trimethyl borate (28.1 g, 270.3 mmol) is added slowly over a 40 minute period. The reaction mixture is warmed to room temperature overnight. 2N HCl (250 mL) is added slowly and the resulting mixture is stirred for 1 hour. The organic layer is separated and the aqueous layer is extracted with ether (2×200 mL). The combined organic layers are dried over anhydrous Na2SO4 and the solvents are removed in vacuo. Hexane (400 mL) is added to the residue and a white precipitate is formed. Filtration and drying in vacuo give 2,6-diethylphenyl boronic acid as a white solid. 1H NMR: (CDCl3) 7.22 (t, 1H), 7.04 (s, 2H), 4.65 (s, 2H), 2.64 (q, 4H), 1.22 (t, 6H). After addition The reaction mixture is warmed to room temperature overnight the resulting mixture is stirred for 1 hour The organic layer is separated the aqueous layer is extracted with ether (2×200 mL) The combined organic layers are dried over anhydrous Na2SO4 the solvents are removed in vacuo Hexane (400 mL) is added to the residue a white precipitate is formed Filtration drying in vacuo

反应条件: temp:-75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,6-Diethyl bromobenzene (38.2 g, 180.2 mmol) is added dropwise through an additional funnel over a 1 hour period to a solution of n-BuLi (2.0 M in cyclohexane, 99.1 mL, 198.2 mmol) in THF (380 mL) at −75° C. After addition, the reaction mixture is stirred at −75° C. for 30 min; trimethyl borate (28.1 g, 270.3 mmol) is added slowly over a 40 minute period. The reaction mixture is warmed to room temperature overnight. 2N HCl (250 mL) is added slowly and the resulting mixture is stirred for 1 hour. The organic layer is separated and the aqueous layer is extracted with ether (2×200 mL). The combined organic layers are dried over anhydrous Na2SO4 and the solvents are removed in vacuo. Hexane (400 mL) is added to the residue and a white precipitate is formed. Filtration and drying in vacuo give 2,6-diethylphenyl boronic acid as a white solid. 1H NMR: (CDCl3) 7.22 (t, 1H), 7.04 (s, 2H), 4.65 (s, 2H), 2.64 (q, 4H), 1.22 (t, 6H). After addition The reaction mixture is warmed to room temperature overnight the resulting mixture is stirred for 1 hour The organic layer is separated the aqueous layer is extracted with ether (2×200 mL) The combined organic layers are dried over anhydrous Na2SO4 the solvents are removed in vacuo Hexane (400 mL) is added to the residue a white precipitate is formed Filtration drying in vacuo

反应条件: temp:-75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,6-Diethyl bromobenzene (38.2 g, 180.2 mmol) is added dropwise through an additional funnel over a 1 hour period to a solution of n-BuLi (2.0 M in cyclohexane, 99.1 mL, 198.2 mmol) in THF (380 mL) at −75° C. After addition, the reaction mixture is stirred at −75° C. for 30 minutes; trimethyl borate (28.1 g, 270.3 mmol) is added slowly over a 40 minute period. The reaction mixture is warmed to room temperature overnight. 2N HCl (250 mL) is added slowly and the resulting mixture is stirred for 1 hour. The organic layer is separated and the aqueous layer is extracted with ether (2×200 mL). The combined organic layers are dried over anhydrous Na2SO4 and the solvents are removed in vacuo. Hexane (400 mL) is added to the residue and a white precipitate is formed. Filtration and drying in vacuo give 2,6-diethylphenyl boronic acid as a white solid. 1H NMR: (CDCl3) 7.22 (t, 1H), 7.04 (s, 2H), 4.65 (s, 2H), 2.64 (q, 4H), 1.22 (t, 6H). After addition The reaction mixture is warmed to room temperature overnight the resulting mixture is stirred for 1 hour The organic layer is separated the aqueous layer is extracted with ether (2×200 mL) The combined organic layers are dried over anhydrous Na2SO4 the solvents are removed in vacuo Hexane (400 mL) is added to the residue a white precipitate is formed Filtration drying in vacuo

反应条件: temp:-75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,6-Diethyl bromobenzene (38.2 g, 180.2 mmol) is added dropwise through an additional funnel over a 1 hour period to a solution of n-BuLi (2.0 M in cyclohexane, 99.1 mL, 198.2 mmol) in THF (380 mL) at −75° C. After addition, the reaction mixture is stirred at −75° C. for 30 minutes; trimethyl borate (28.1 g, 270.3 mmol) is added slowly over a 40 minute period. The reaction mixture is warmed to room temperature overnight. 2N HCl (250 mL) is added slowly and the resulting mixture is stirred for 1 hour. The organic layer is separated and the aqueous layer is extracted with ether (2×200 mL). The combined organic layers are dried over anhydrous Na2SO4 and the solvents are removed in vacuo. Hexane (400 mL) is added to the residue and a white precipitate is formed. Filtration and drying in vacuo give 2,6-diethylphenyl boronic acid as a white solid. 1H NMR: (CDCl3) 7.22 (t, 1H), 7.04 (s, 2H), 4.65 (s, 2H), 2.64 (q, 4H), 1.22 (t, 6H). After addition The reaction mixture is warmed to room temperature overnight the resulting mixture is stirred for 1 hour The organic layer is separated the aqueous layer is extracted with ether (2×200 mL) The combined organic layers are dried over anhydrous Na2SO4 the solvents are removed in vacuo Hexane (400 mL) is added to the residue a white precipitate is formed Filtration drying in vacuo

反应条件: temp:-75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,6-Diethyl bromobenzene (38.2 g, 180.2 mmol) is added dropwise through an additional funnel over a 1 hour period to a solution of n-BuLi (2.0 M in cyclohexane, 99.1 ml, 198.2 mmol) in THF (380 mL) at −75° C. After addition, the reaction mixture is stirred at −75° C. for 30 minutes; trimethyl borate (28.1 g, 270.3 mmol) is added slowly over a 40 minute period. The reaction mixture is warmed to room temperature overnight. 2N HCl (250 mL) is added slowly and the resulting mixture is stirred for 1 hour. The organic layer is separated and the aqueous layer is extracted with ether (2×200 mL). The combined organic layers are dried over anhydrous Na2SO4 and the solvents are removed in vacuo. Hexane (400 mL) is added to the residue and a white precipitate is formed. Filtration and drying in vacuo gives 19.0 g of 2,6-diethylphenyl boronic acid as a white solid. 1H NMR: (CDCl3) 7.22 (t, 1H), 7.04 (s, 2H), 4.65 (s, 2H), 2.64 (q, 4H), 1.22 (t, 6H). After addition The reaction mixture is warmed to room temperature overnight the resulting mixture is stirred for 1 hour The organic layer is separated the aqueous layer is extracted with ether (2×200 mL) The combined organic layers are dried over anhydrous Na2SO4 the solvents are removed in vacuo Hexane (400 mL) is added to the residue a white precipitate is formed Filtration drying in vacuo

反应条件: temp:-75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,6-Diethyl bromobenzene (38.2 g, 180.2 mmol) is added dropwise through an additional funnel over a 1 hour period to a solution of n-BuLi (2.0 M in cyclohexane, 99.1 ml, 198.2 mmol) in THF (380 mL) at −75° C. After addition, the reaction mixture is stirred at −75° C. for 30 minutes; trimethyl borate (28.1 g, 270.3 mmol) is added slowly over a 40 minute period. The reaction mixture is warmed to room temperature overnight. 2N HCl (250 mL) is added slowly and the resulting mixture is stirred for 1 hour. The organic layer is separated and the aqueous layer is extracted with ether (2×200 mL). The combined organic layers are dried over anhydrous Na2SO4 and the solvents are removed in vacuo. Hexane (400 mL) is added to the residue and a white precipitate is formed. Filtration and drying in vacuo gives 19.0 g of 2,6-diethylphenyl boronic acid as a white solid. 1H NMR: (CDCl3) 7.22 (t, 1H), 7.04 (s, 2H), 4.65 (s, 2H), 2.64 (q, 4H), 1.22 (t, 6H). After addition The reaction mixture is warmed to room temperature overnight the resulting mixture is stirred for 1 hour The organic layer is separated the aqueous layer is extracted with ether (2×200 mL) The combined organic layers are dried over anhydrous Na2SO4 the solvents are removed in vacuo Hexane (400 mL) is added to the residue a white precipitate is formed Filtration drying in vacuo

反应条件: temp:-75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,6-Diethyl bromobenzene (38.2 g, 180.2 mmol) is added dropwise through an additional funnel over a 1 hour period to a solution of n-BuLi (2.0 M in cyclohexane, 99.1 mL, 198.2 mmol) in THF (380 mL) at −75° C. After addition, the reaction mixture is stirred at −75° C. for 30 minutes; trimethyl borate (28.1 g, 270.3 mmol) is added slowly over a 40 minute period. The reaction mixture is warmed to room temperature overnight. 2N HCl (250 mL) is added slowly and the resulting mixture is stirred for 1 hour. The organic layer is separated and the aqueous layer is extracted with ether (2×200 mL). The combined organic layers are dried over anhydrous Na2SO4 and the solvents are removed in vacuo. Hexane (400 mL) is added to the residue and a white precipitate is formed. Filtration and drying in vacuo give 2,6-diethylphenyl boronic acid as a white solid. 1H NMR: (CDCl3) 7.22 (t, 1H), 7.04 (s, 2H), 4.65 (s, 2H), 2.64 (q, 4H), 1.22 (t, 6H). After addition The reaction mixture is warmed to room temperature overnight the resulting mixture is stirred for 1 hour The organic layer is separated the aqueous layer is extracted with ether (2×200 mL) The combined organic layers are dried over anhydrous Na2SO4 the solvents are removed in vacuo Hexane (400 mL) is added to the residue a white precipitate is formed Filtration drying in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1,3-diethyl-2-bromobenzene (3.87 g, 18.2 mmol), 3-formylphenylboronic acid (3.0 g, 20.0 mmol), tetrakistriphenylphosphinepalladium (0.84 g, 0.73 mmol), sodium carbonate (5.79 g, 54.6 mmol), water (20 mL), ethanol (20 mL) and toluene (200 mL) was heated under reflux overnight under an argon atmosphere. The reaction mixture was cooled, diluted with ethyl acetate, washed with water, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=5/1) to give the title compound (3.48 g, yield 81%) as a yellow oil. was heated under reflux overnight under an argon atmosphere The reaction mixture was cooled washed with water dried concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=5/1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1,3-diethyl-2-bromobenzene (3.87 g, 18.2 mmol), 3-formylphenylboronic acid (3.0 g, 20.0 mmol), tetrakistriphenylphosphinepalladium (0.84 g, 0.73 mmol), sodium carbonate (5.79 g, 54.6 mmol), water (20 mL), ethanol (20 mL) and toluene (200 mL) was heated under reflux overnight under an argon atmosphere. The reaction mixture was cooled, diluted with ethyl acetate, washed with water, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=5/1) to give the title compound (3.48 g, yield 81%) as a yellow oil. was heated under reflux overnight under an argon atmosphere The reaction mixture was cooled washed with water dried concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=5/1)

反应条件: temp:-75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,6-Diethyl bromobenzene (38.2 g, 180.2 mmol) is added dropwise through an additional funnel over a 1 h period to a solution of n-BuLi (2.0 M in cyclohexane, 99.1 mL, 198.2 mmol) in THF (380 mL) at −75° C. After addition, the reaction mixture is stirred at −75° C. for 30 min; trimethyl borate (28.1 g, 270.3 mmol) is added slowly over a 40 minute period. The reaction mixture is warmed to room temperature overnight. 2N HCl (250 mL) is added slowly and the resulting mixture is stirred for 1 h. The organic layer is separated and the aqueous layer is extracted with ether (2×200 mL). The combined organic layers are dried over anhydrous Na2SO4 and the solvents are removed in vacuo. Hexane (400 mL) is added to the residue and a white precipitate is formed. Filtration and drying in vacuo give 2,6-diethylphenyl boronic acid as a white solid. 1H NMR: (CDCl3) 7.22 (t, 1H), 7.04 (s, 2H), 4.65 (s, 2H), 2.64 (q, 4H), 1.22 (t, 6H). After addition The reaction mixture is warmed to room temperature overnight the resulting mixture is stirred for 1 h The organic layer is separated the aqueous layer is extracted with ether (2×200 mL) The combined organic layers are dried over anhydrous Na2SO4 the solvents are removed in vacuo Hexane (400 mL) is added to the residue a white precipitate is formed Filtration drying in vacuo

反应条件: temp:-75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,6-Diethyl bromobenzene (38.2 g, 180.2 mmol) is added dropwise through an additional funnel over a 1 hour period to a solution of n-BuLi (2.0 M in cyclohexane, 99.1 ml, 198.2 mmol) in THF (380 mL) at −75° C. After addition, the reaction mixture is stirred at −75° C. for 30 minutes; trimethyl borate (28.1 g, 270.3 mmol) is added slowly over a 40 minute period. The reaction mixture is warmed to room temperature overnight. 2N HCl (250 mL) is added slowly and the resulting mixture is stirred for 1 hour. The organic layer is separated and the aqueous layer is extracted with ether (2×200 mL). The combined organic layers are dried over anhydrous Na2SO4 and the solvents are removed in vacuo. Hexane (400 mL) is added to the residue and a white precipitate is formed. Filtration and drying in vacuo gives 19.0 g of 2,6-diethylphenyl boronic acid as a white solid. 1H NMR: (CDCl3) 7.22 (t, 1H), 7.04 (s, 2H), 4.65 (s, 2H), 2.64 (q, 4H), 1.22 (t, 6H). After addition The reaction mixture is warmed to room temperature overnight the resulting mixture is stirred for 1 hour The organic layer is separated the aqueous layer is extracted with ether (2×200 mL) The combined organic layers are dried over anhydrous Na2SO4 the solvents are removed in vacuo Hexane (400 mL) is added to the residue a white precipitate is formed Filtration drying in vacuo