Benzyl Alcohol → 1-(Benzyloxy)-3-bromo-5-fluorobenzene

Participants

Reaction Steps

Sodium hydride (60% w/w dispersion in mineral oil) 10.3 g was added portion-wise to a solution of benzyl alcohol (28.8 ml) in dimethylacetamide (400 ml) and the mixture stirred at room temperature for about 1 hour. 1-Bromo-3,5-difluorobenzene (50 g) was added dropwise. The mixture was stirred at room temperature for about 2 hours and the solvent was evaporated in vacuo. The residue was partitioned between methylene chloride and water and the organic phase was washed with water, dried over sodium sulfate and evaporated to give 90 g of crude product which was purified on silica gel eluting with methylene chloride/hexanes to give 47.7 g of the title compound as an oil.

Provenance & Evidence