3-Bromothiophene → (4-Bromophenyl)(thiophen-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.5M BuLi in hexanes (3.5 mL, 5.25 mmol) in THF (6.5 mL) cooled to −78° C. was added 3-bromothiophene dropwise (469 μL, 5.0 mmol). The mixture was stirred for 30 minutes and a 1.0M solution of 4-bromobenzaldehyde in THF was slowly added (5.5 mL, 5.5 mmol). The reaction was warmed to 0° C. and aged for 1 hour. The mixture was then poured into a saturated aqueous solution of NH4Cl. The resulting mixture was extracted 3 times with ethyl acetate and the organic layers were washed with brine, dried and evaporated. The crude residue was chromatographed on silica gel using a gradient of 10-25% ethyl acetate in hexanes to afford the title compound.

Provenance & Evidence