1-(2-bromo-5-fluorophenyl)ethanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromo-5-fluoro-benzaldehyde (17.0 g, 83.7 mmol) in tetrahydrofuran (100 mL), cooled to 0° C. under nitrogen, was added methyl magnesium chloride solution (3M in tetrahydrofuran, 31.0 mL, 93.0 mmol, 1.1 eq.) dropwise over a 20 min period. The resulting solution was stirred at 0° C. for 45 min before quenching with aqueous ammonium chloride solution (1M, 17 mL). The resulting mixture was partitioned between pentane (300 mL) and water (100 mL). The organic phase was washed with brine (50 mL) and then dried over magnesium sulphate. This mixture was filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with a gradient of toluene in pentane (50:50 to 100:0 by volume) to produce the title compound as a colourless oil (13.8 g, 75%). before quenching with aqueous ammonium chloride solution (1M, 17 mL) The resulting mixture was partitioned between pentane (300 mL) and water (100 mL) The organic phase was washed with brine (50 mL) dried over magnesium sulphate This mixture was filtered concentrated under reduced pressure The residue was purified by chromatography on silica gel eluting with a gradient of toluene in pentane (50:50 to 100:0 by volume)