Dimethylformamide → 5-Bromo-2-fluoro-3-methylbenzaldehyde

Participants

Reaction Steps

To a solution of 5-bromo-2-fluorotoluene 169 (1.0 g, 5.29 mmol.) in anhydrous THF (4 mL) cooled in dry ice/acetone bath was added a 2 M solution of lithium diisopropylamide (2.6 mL, 5.2 mmol.). The reaction mixture was stirred for 1 hour in the dry ice/acetone bath. Anhydrous dimethylformamide (0.46 g, 6.35 mmol.) was added in a dropwise manner. The reaction mixture was allowed to warm to room temperature in 3 hours. Ethyl acetate (100 mL) was added. The organic layer was washed with 1 N hydrochloric acid, water and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure to afford 5-bromo-2-fluoro-3-methylbenzaldehyde 170 (1.08 g, 4.98 mmol.). The crude product was used in the next step without further purification.

Provenance & Evidence