3-Chlorobenzaldehyde → (4-Bromo-3-thienyl)(3-chlorophenyl)methanol

Participants

Reaction Conditions

Reaction Steps

3,4-Dibromothiophene (15.5 g, 64.1 mmol) was added dropwise to a solution of n-BuLi (2.5M in hexane, 25.6 mL, 64.1 mmol) in Et2O (50 mL) at −78° C. After 1.5 h, 3-chlorobenzaldehyde (7.29 mL, 64.1 mmol) was added dropwise to the beige suspension. The resulting solution was stirred at −78° C. for 1 h and allowed to warm to 0° C. After 1 h, the reaction was quenched by the addition of 25% aq. NH4OAc. The aqueous layer was extracted with EtOAc and the combined organics were washed with water and brine, dried (Na2SO4) and concentrated to afford the desired product as a pale yellow oil. The crude product was used directly without further purification.

Provenance & Evidence