1-(2-氯苯基)丙烷-1,2-二酮

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1-(2-chlorophenyl)propane-1,2-dione (4.2379 g, 23.208 mmol), bromine (1.1891 mL, 23.208 mmol), and glacial acetic acid (0.67005 mL, 11.604 mmol) in chloroform (58.020 mL, 23.208 mmol) was heated at 60° C. After 17 h of stirring at 60° C., the mixture was removed from heat and concentrated under reduced pressure to give 3-bromo-1-(2-chlorophenyl)propane-1,2-dione as an orange liquid: LC-MS: a peak of m/z 261.0 [M+H(79Br)]+ and 262.9 [M+H (81Br)-]+. The orange liquid was carried on crude without purification for the next step. the mixture was removed from heat concentrated under reduced pressure

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

实验步骤: To a solution of 2-chlorophenylacetone (10.800 g, 64.049 mmol) in 279 mL of CH2Cl2, pyridinium chlorochromate (41.418 g, 192.15 mmol), and pyridine (16 mL) in three portions were added over 2.5 hours and the mixture was refluxed under vigorous stirring. After 22 h, the mixture was removed from heat. The mixture was concentrated in vacuo to give a dark red syrup. The crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column using 0-10% gradient of EtOAc in hexane over 28 min as eluent to give 1-(2-chlorophenyl)propane-1,2-dione as yellow liquid: 1H NMR (400 MHz, choroform-d) δ ppm 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.49-7.54 (1H, m), 7.38-7.45 (2H, m), 2.58 (3H, s); LC-MS: m/z 182.9 [N+H]+. the mixture was refluxed under vigorous stirring the mixture was removed from heat The mixture was concentrated in vacuo to give a dark red syrup The crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column over 28 min

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1-(2-chlorophenyl)propane-1,2-dione (1.2592 g, 6.9 mmol), glacial acetic acid (0.20 mL, 3.4 mmol, 0.5 eq), and bromine (0.35 mL, 6.8 mmol, 1 eq) in CHCl3 (17 mL) was heated at 60° C. for 12 h. The mixture was concentrated under reduced pressure to provide 3-bromo-1-(2-chlorophenyl)propane-1,2-dione as yellow liquid. The yellow liquid was carried on crude without purification for the next step. 1H NMR (CDCl3) δ ppm 7.71 (1H, dd, J=7.8, 1.6 Hz), 7.53-7.59 (1H, m), 7.40-7.49 (2H, m), 4.52 (2H, s). Mass Spectrum (ESI) m/e=261.0 [M+1 (79Br)] and 262.9 [M+1 (81Br)]. The mixture was concentrated under reduced pressure

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

实验步骤: To a solution of 2-chlorophenylacetone (7.14 g, 42 mmol) in CH2Cl2 (184 mL), PCC (27 g, 127 mmol, 3 eq) and pyridine (10 mL, 127 mmol, 3 eq) in three portions were added over five hours at reflux under vigorous stirring. After the addition was complete, the mixture was further refluxed under vigorous stirring for 21.5 h. The mixture was filtered through a pad of silica gel, washed the pad with CH2Cl2, and concentrated under reduced pressure to provide a dark red syrup. The residue was purified by column chromatography on a 120 g of Redi-Sep™ column using 0-15% gradient of EtOAc in hexane over 40 min as eluent to provide 1-(2-chlorophenyl)propane-1,2-dione as yellow liquid. 1H NMR (choroform-d) δ ppm 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.48-7.54 (1H, m), 7.37-7.46 (2H, m), 2.58 (3H, s). Mass Spectrum (ESI) m/e=182.9 (M+1). at reflux under vigorous stirring After the addition the mixture was further refluxed The mixture was filtered through a pad of silica gel washed the pad with CH2Cl2 concentrated under reduced pressure to provide a dark red syrup The residue was purified by column chromatography on a 120 g of Redi-Sep™ column over 40 min

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1-(2-chlorophenyl)propane-1,2-dione (4.2379 g, 23.208 mmol), bromine (1.1891 mL, 23.208 mmol), and glacial acetic acid (0.67005 mL, 11.604 mmol) in chloroform (58.020 mL, 23.208 mmol) was heated at 60° C. After 17 h of stirring at 60° C., the mixture was removed from heat and concentrated under reduced pressure to give 3-bromo-1-(2-chlorophenyl)propane-1,2-dione as an orange liquid: LC-MS: a peak of m/z 261.0 [M+H(79Br)]+ and 262.9 [M+H (81Br)-]+. The orange liquid was carried on crude without purification for the next step. the mixture was removed from heat concentrated under reduced pressure

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

实验步骤: To a solution of 2-chlorophenylacetone (10.800 g, 64.049 mmol) in 279 mL of CH2Cl2, pyridinium chlorochromate (41.418 g, 192.15 mmol), and pyridine (16 mL) in three portions were added over 2.5 hours and the mixture was refluxed under vigorous stirring. After 22 h, the mixture was removed from heat. The mixture was concentrated in vacuo to give a dark red syrup. The crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column using 0-10% gradient of EtOAc in hexane over 28 min as eluent to give 1-(2-chlorophenyl)propane-1,2-dione as yellow liquid: 1H NMR (400 MHz, choroform-d) δ ppm 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.49-7.54 (1H, m), 7.38-7.45 (2H, m), 2.58 (3H, s); LC-MS: m/z 182.9 [N+H]+. the mixture was refluxed under vigorous stirring the mixture was removed from heat The mixture was concentrated in vacuo to give a dark red syrup The crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column over 28 min

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1-(2-chlorophenyl)propane-1,2-dione (1.2592 g, 6.9 mmol), glacial acetic acid (0.20 mL, 3.4 mmol, 0.5 eq), and bromine (0.35 mL, 6.8 mmol, 1 eq) in CHCl3 (17 mL) was heated at 60° C. for 12 h. The mixture was concentrated under reduced pressure to provide 3-bromo-1-(2-chlorophenyl)propane-1,2-dione as yellow liquid. The yellow liquid was carried on crude without purification for the next step. 1H NMR (CDCl3) δ ppm 7.71 (1H, dd, J=7.8, 1.6 Hz), 7.53-7.59 (1H, m), 7.40-7.49 (2H, m), 4.52 (2H, s). Mass Spectrum (ESI) m/e=261.0 [M+1 (79Br)] and 262.9 [M+1 (81Br)]. The mixture was concentrated under reduced pressure

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

实验步骤: To a solution of 2-chlorophenylacetone (7.14 g, 42 mmol) in CH2Cl2 (184 mL), PCC (27 g, 127 mmol, 3 eq) and pyridine (10 mL, 127 mmol, 3 eq) in three portions were added over five hours at reflux under vigorous stirring. After the addition was complete, the mixture was further refluxed under vigorous stirring for 21.5 h. The mixture was filtered through a pad of silica gel, washed the pad with CH2Cl2, and concentrated under reduced pressure to provide a dark red syrup. The residue was purified by column chromatography on a 120 g of Redi-Sep™ column using 0-15% gradient of EtOAc in hexane over 40 min as eluent to provide 1-(2-chlorophenyl)propane-1,2-dione as yellow liquid. 1H NMR (choroform-d) δ ppm 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.48-7.54 (1H, m), 7.37-7.46 (2H, m), 2.58 (3H, s). Mass Spectrum (ESI) m/e=182.9 (M+1). at reflux under vigorous stirring After the addition the mixture was further refluxed The mixture was filtered through a pad of silica gel washed the pad with CH2Cl2 concentrated under reduced pressure to provide a dark red syrup The residue was purified by column chromatography on a 120 g of Redi-Sep™ column over 40 min

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1-(2-chlorophenyl)propane-1,2-dione (4.2379 g, 23.208 mmol), bromine (1.1891 mL, 23.208 mmol), and glacial acetic acid (0.67005 mL, 11.604 mmol) in chloroform (58.020 mL, 23.208 mmol) was heated at 60° C. After 17 h of stirring at 60° C., the mixture was removed from heat and concentrated under reduced pressure to give 3-bromo-1-(2-chlorophenyl)propane-1,2-dione as an orange liquid: LC-MS: a peak of m/z 261.0 [M+H(79Br)]+ and 262.9 [M+H (81Br)−]+. The orange liquid was carried on crude without purification for the next step. the mixture was removed from heat concentrated under reduced pressure

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

实验步骤: To a solution of 2-chlorophenylacetone (10.800 g, 64.049 mmol) in 279 mL of CH2Cl2, pyridinium chlorochromate (41.418 g, 192.15 mmol), and pyridine (16 mL) in three portions were added over 2.5 hours and the mixture was refluxed under vigorous stirring. After 22 h, the mixture was removed from heat. The mixture was concentrated in vacuo to give a dark red syrup. The crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column using 0-10% gradient of EtOAc in hexane over 28 min as eluent to give 1-(2-chlorophenyl)propane-1,2-dione as yellow liquid: 1H NMR (400 MHz, chloroform-d) δ ppm 7.66 (1 H, dd, J=7.6, 1.8 Hz), 7.49-7.54 (1 H, m), 7.38-7.45 (2 H, m), 2.58 (3 H, s); LC-MS: m/z 182.9 [M+H]+. the mixture was refluxed under vigorous stirring the mixture was removed from heat The mixture was concentrated in vacuo to give a dark red syrup The crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column over 28 min