Dimethylformamide → 2-Bromo-6-fluorobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of diisopropylamine (7.9 mL, 55 mmol) in anhydrous tetrahydrofuran (70 mL) cooled to 0° C. was treated dropwise with butyllithium (1.6 M in hexanes, 34.9 mL, 56 mmol). The mixture was stirred at 0° C. for 15 min, then it was cooled to −78° C., and 1-bromo-3-fluoro-benzene (6.1 mL, 56 mmol) was added over 10 min. The mixture was stirred at −78° C. for 1 h, then anhydrous N,N-dimethylformamide (4.9 mL, 64 mmol) was added dropwise over 5 min. The mixture was stirred for another 20 min, then acetic acid (8 mL) and water (180 mL) were added, warmed up to RT, and extracted with ethyl acetate (2×175 mL). The combined organic layers were washed with water (2×75 mL), brine (100 mL), dried over anhydrous sodium sulfate, and concentrated to yield the crude product which was purified by silica gel chromatography (20-30% EtOAc in hexanes) to give 2-bromo-6-fluorobenzaldehyde as a pale yellow solid. MS (ESI, pos. ion) m/z: 204 (M+1).

Provenance & Evidence