Methyl chloroformate → 3-Bromo-4-fluorobenzyl Alcohol

Participants

Reaction Steps

2 g of triethylamine, dissolved in 5 ml of tetrahydrofuran, were added dropwise to a solution of 4.2 g of 3-bromo-4-fluoro-benzoic acid and 1.95 g of chloroformic acid methyl ester in 30 ml of tetrahydrofuran at 20° C., while stirring. Stirring was continued for a further 40 minutes at 20°-25° C. and the hydrochloride which had precipitated was then filtered off. 5.5 g of sodium borohydride, dissolved in 20 ml of water, were added dropwise to the filtrate at 10° to 20° C., while stirring. Stirring was then continued for a further 4 hours at 20° C. The reaction batch was subsequently poured into 100 ml of water and extracted by shaking with 80 ml of methylene chloride. The methylene chloride phase was separated off and dried over magnesium sulphate and the solvent was then distilled off in vacuo. 1.95 g (95% of theory) of 3-bromo-4-fluoro-benzyl alcohol were obtained as a colorless oil.

Provenance & Evidence