5-Bromo-2-fluorobenzaldehyde → (5-Bromo-2-fluorophenyl)methanol

Participants

Reaction Steps

5-Bromo-2-fluorobenzaldehyde (commercially available from Aldrich) (150.0 g, 739 mmol) was charged into a 2 liter round bottom flask. The reaction mixture in the flask was immersed in an ice-water bath. Methylmagnesium bromide (270 mL, 812 mmol) was added dropwise via an addition funnel. The reaction mixture was stirred for one hour following completion of the addition. After the reaction was completed, the mixture was slowly poured into 500 mL ice water and 250 mL saturated ammonium chloride. The resulting aqueous solution was extracted with ether (800 mL×2) in a separation funnel. The combined ether layer was washed with brine and dried over sodium sulfate. Removal of the solvent gave the product (150 g, yield=93%). The product was used directly in the next step without further purification.

Provenance & Evidence