Dimethylformamide → 2,6-Difluoro-3-(phenylmethoxy)benzaldehyde

Participants

Reaction Steps

To 1-Benzyloxy-2,4-difluoro-benzene (26, 3.00 g, 13.6 mmol) in tetrahydrofuran (48 mL) under an atmosphere of nitrogen and cooled with dry ice/acetone was added n-butyllithium (1.60 M in hexane, 8.94 mL). After 20 minutes, N,N-dimethylformamide (1.46 mL, 0.0189 mol) was added to the reaction. After another 20 minutes, the flask was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, acidified to pH=1, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified with silica gel column chromatography eluting with 30% ethyl acetate in hexane to give the compound as a yellow solid (27, 2.5 g, 74%).

Provenance & Evidence