4-溴-2-(羟甲基)苄醇

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound of example 669 (7 g, 32.25 mmol), 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane (9.63 g, 38.70 mmol) and [1,1-Bis(diphenylphosphino)-ferrocine]dichloropalladium(II), complex with dichloromethane (789 mg, 0.967 mmol) were taken in dry DMF under Argon atmosphere. Degassed 2M solution of sodium carbonate (8.54 g, 80.62 mmol) was added and the reaction mixture was heated to 80° C. for 3 h. The reaction mixture was cooled and the solvent was removed by distillation. The residue was taken in water and the aqueous mixture was extracted with ethyl acetate. The crude material obtained was purified using column chromatography (silicagel, 30% dichloromethane in petroleum ether) to afford the title compound. was added The reaction mixture was cooled the solvent was removed by distillation the aqueous mixture was extracted with ethyl acetate The crude material obtained was purified

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound of example 668 (2 g, 7.326 mmol) was taken in dry THF and was added to a slurry of LiAlH4 (1.67 g, 43.95 mmol) in THF cooled to 0° C. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with aqueous NaOH solution followed by extraction with ethyl acetate. The solvent was removed by distillation to afford the title compound. The reaction mixture was quenched with aqueous NaOH solution followed by extraction with ethyl acetate The solvent was removed by distillation

反应条件: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Lithium aluminumhydride (320 mg, 8.81 mmol) was added to a solution of 5-bromoisobenzofuran-1,3-dione (1 g, 4.4 mmol) in THF at room temperature. The mixture was heated at reflux for 3 h, cooled to −30° C., and then quenched with water. The mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to afford the title compound (1.2 g). 1HNMR (400 MHz, DMSO-d6): δ 7.54 (d, 1H), 7.42 (dd, 1H), 7.33-7.31 (m, 1H), 5.23 (t, 1H), 5.15 (t, 1H), 4.51 (d, 2H), 4.45 (d, 2H). The mixture was heated at reflux for 3 h quenched with water The mixture was extracted with EtOAc The organic layer was dried over MgSO4 concentrated

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound of example 669 (7 g, 32.25 mmol), 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane (9.63 g, 38.70 mmol) and [1,1-Bis(diphenylphosphino)-ferrocine]dichloropalladium(II), complex with dichloromethane (789 mg, 0.967 mmol) were taken in dry DMF under Argon atmosphere. Degassed 2M solution of sodium carbonate (8.54 g, 80.62 mmol) was added and the reaction mixture was heated to 80° C. for 3 h. The reaction mixture was cooled and the solvent was removed by distillation. The residue was taken in water and the aqueous mixture was extracted with ethyl acetate. The crude material obtained was purified using column chromatography (silicagel, 30% dichloromethane in petroleum ether) to afford the title compound. was added The reaction mixture was cooled the solvent was removed by distillation the aqueous mixture was extracted with ethyl acetate The crude material obtained was purified

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound of example 669 (7 g, 32.25 mmol), 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane (9.63 g, 38.70 mmol) and [1,1-Bis(diphenylphosphino)-ferrocine]dichloropalladium(II), complex with dichloromethane (789 mg, 0.967 mmol) were taken in dry DMF under Argon atmosphere. Degassed 2M solution of sodium carbonate (8.54 g, 80.62 mmol) was added and the reaction mixture was heated to 80° C. for 3 h. The reaction mixture was cooled and the solvent was removed by distillation. The residue was taken in water and the aqueous mixture was extracted with ethyl acetate. The crude material obtained was purified using column chromatography (silicagel, 30% dichloromethane in petroleum ether) to afford the title compound. was added The reaction mixture was cooled the solvent was removed by distillation the aqueous mixture was extracted with ethyl acetate The crude material obtained was purified

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound of example 668 (2 g, 7.326 mmol) was taken in dry THF and was added to a slurry of LiAlH4 (1.67 g, 43.95 mmol) in THF cooled to 0° C. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with aqueous NaOH solution followed by extraction with ethyl acetate. The solvent was removed by distillation to afford the title compound. The reaction mixture was quenched with aqueous NaOH solution followed by extraction with ethyl acetate The solvent was removed by distillation

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

实验步骤: To a solution of 4-bromophthalic acid (3.0 g, 12.24 mmol) in 30 mL of THF was added a solution of borane-THF complex (1.0M) dropwise at 0° C. The solution was warmed to rt and stirred for 3 h. The reaction mixture was quenched by addition of HCl (2N) at 0° C. The product was extracted with ethyl acetate and washed with sat. NaCl, dried over Na2SO4, and concentrated under reduced pressure to afford 2.8 g (100%) of 4-bromo-2-hydroxymethylbenzyl alcohol as a colorless oil. 1H NMR (CDCl3) 7.28 (m, 2H), 7.26 (m, 1H), 4.69 (s, 4H), 2.80 (bs, 2H). The reaction mixture was quenched by addition of HCl (2N) at 0° C The product was extracted with ethyl acetate washed with sat. NaCl dried over Na2SO4 concentrated under reduced pressure

反应条件: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Lithium aluminumhydride (320 mg, 8.81 mmol) was added to a solution of 5-bromoisobenzofuran-1,3-dione (1 g, 4.4 mmol) in THF at room temperature. The mixture was heated at reflux for 3 h, cooled to −30° C., and then quenched with water. The mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to afford the title compound (1.2 g). 1HNMR (400 MHz, DMSO-d6): δ 7.54 (d, 1H), 7.42 (dd, 1H), 7.33-7.31 (m, 1H), 5.23 (t, 1H), 5.15 (t, 1H), 4.51 (d, 2H), 4.45 (d, 2H). The mixture was heated at reflux for 3 h quenched with water The mixture was extracted with EtOAc The organic layer was dried over MgSO4 concentrated

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound of example 669 (7 g, 32.25 mmol), 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane (9.63 g, 38.70 mmol) and [1,1-Bis(diphenylphosphino)-ferrocine]dichloropalladium(II), complex with dichloromethane (789 mg, 0.967 mmol) were taken in dry DMF under Argon atmosphere. Degassed 2M solution of sodium carbonate (8.54 g, 80.62 mmol) was added and the reaction mixture was heated to 80° C. for 3 h. The reaction mixture was cooled and the solvent was removed by distillation. The residue was taken in water and the aqueous mixture was extracted with ethyl acetate. The crude material obtained was purified using column chromatography (silicagel, 30% dichloromethane in petroleum ether) to afford the title compound. was added The reaction mixture was cooled the solvent was removed by distillation the aqueous mixture was extracted with ethyl acetate The crude material obtained was purified

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound of example 668 (2 g, 7.326 mmol) was taken in dry THF and was added to a slurry of LiAlH4 (1.67 g, 43.95 mmol) in THF cooled to 0° C. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with aqueous NaOH solution followed by extraction with ethyl acetate. The solvent was removed by distillation to afford the title compound. The reaction mixture was quenched with aqueous NaOH solution followed by extraction with ethyl acetate The solvent was removed by distillation