Water → Benzyl (2,4-difluoro-3-formylphenyl)carbamate

Participants

Reaction Conditions

Reaction Steps

Into a round bottom flask was added (2,4-difluoro-phenyl)-carbamic acid benzyl ester (3, 3.83 g, 14.5 mmol) in 148 mL of tetrahydrofuran. The solution was chilled to −78° C. and n-butyllithium (1.60 M in hexane, 19.1 mL, 30.0 mmol) was added over 30 minutes followed by the addition of 1.12 mL of N,N-dimethylformamide. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into water and extracted with ethyl acetate and the organic layer was washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum and crystallized from ether to give the desired compound (4, 3.0 g, 71%).

Provenance & Evidence