1-(3-bromo-5-fluorophenyl)ethanone

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(3-bromo-5-fluoro-phenyl)-ethanol (2.9 g, 13.2 mmol) in methylene chloride (150 ml) was added at room temperature pyridinium dichromate (3.98 g). The reaction mixture was stirred for 4 hours at room temperature and the solvent was removed in the presence of silica gel. The crude product was purified by chromatography over silica gel to provide 1-(3-bromo-5-fluoro-phenyl)-ethanone (1.39 g, 45%) as a light yellow solid, MS: m/e=216.1 (M+). the solvent was removed in the presence of silica gel The crude product was purified by chromatography over silica gel

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyllithium (1.3 M in diethyl ether, 35 mL) was added dropwise to 3-bromo-5-fluorobenzoic acid (5 g) in diethyl ether at −78° C. keeping the temperature below −60° C. The reaction was then left to warm to −10° C. and was stirred for 1 h before being carefully quenched with saturated ammonium chloride (100 mL) until pH=3. The product was extracted with diethyl ether (2×100 mL), dried over sodium sulfate and the solvent removed by evaporation to yield 1-(3-bromo-5-fluorophenyl)ethanone as an off-white solid (4.67 g, 94%). 1H NMR (CDCl3): 2.59 (3H, s, ArCOCH3), 7.44 (1H, dd, Ar), 7.59 (1H, dd, Ar), 7.87 (1H, s, Ar). the temperature below −60° C The reaction was then left before being carefully quenched with saturated ammonium chloride (100 mL) until pH=3 The product was extracted with diethyl ether (2×100 mL) dried over sodium sulfate the solvent removed by evaporation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(3-bromo-5-fluoro-phenyl)-ethanol (2.9 g, 13.2 mmol) in methylene chloride (150 ml) was added at room temperature pyridinium dichromate (3.98 g). The reaction mixture was stirred for 4 hours at room temperature and the solvent was removed in the presence of silica gel. The crude product was purified by chromatography over silica gel to provide 1-(3-bromo-5-fluoro-phenyl)-ethanone (1.39 g, 45%) as a light yellow solid, MS: m/e=216.1 (M+). the solvent was removed in the presence of silica gel The crude product was purified by chromatography over silica gel