Water → HCID 67185843, compound

Participants

Reaction Conditions

Reaction Steps

21.32 ml (169.9 mmol) of N,N,N,N-tetramethylguanidine are added to a solution, cooled to −70° C., of 30 g (147.8 mmol) of 5-bromo-2-fluorobenzaldehyde and 50.51 g (169.9 mmol) of methyl [(tert-butoxycarbonyl)amino](dimethoxyphosphoryl)acetate in 450 ml anhydrous tetrahydrofuran. After stirring at −70° C. for 4 h, the reaction mixture is stirred at RT for 15 h. 1000 ml of water and 1000 ml of ethyl acetate are added to the mixture. The organic phase is washed with water, dried over sodium sulfate and concentrated. The crude product is purified by column chromatography on silica gel (mobile phase: cyclohexane:ethyl acetate 4:1).

Provenance & Evidence