Sulfuric Acid → 2,6-Difluoro-4-methylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,3-difluoro-5-methylbenzene (10.2 g, 80 mmol) in anhydrous ether (80 mL) was added n-BuLi (2.5 M solution in hexane, 48 ml, 120 mmol) over a 20 min period while the internal temperature was maintained at around −50° C. After stirring at that temperature for 1.5 hr, DMF (14.6 g, 200 mmol) was added over a 20 min period. After stirring at the same temperature for an additional 1.5 h, the reaction mixture was slowly poured into 1N aqueous sulfuric acid (300 mL) and extracted with ether three times. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated to give the title compound (11.2 g, 90%). 1H-NMR (500 MHz, CDCl3): δ 10.25 (s, 1H), 6.75 (d, 2H, J=9.9 Hz), 2.39 (s, 3H).

Provenance & Evidence