Diisopropylamine → 3-Chloro-2,6-difluorobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (1.43M in hexane, 20.2 mmol, 14.1 ml) was added dropwise at 0° C. to a solution of diisopropylamine (2.91 ml, 22.2 mmol) in THF (80 ml). After 30 min. at 0° C., the solution was cooled to -78° C. and 1-chloro-2,4-difluorobenzene (3 g, 20.2 mmol) in THF (10 ml) added dropwise. After 30 min., 4-formylmorpholine (4.1 ml) was added and the mixture warmed to room temperature over 1 h, diluted with 1N HCl, extracted twice with ethyl acetate, the extracts washed with brine, dried over sodium sulphate and evaporated to give a mobile yellow oil (2.2 g), MS (+EI) 178/177/176/175 (M+), 1H NMR (CDCl3) 10.34 (1H, s), 7.66-7.60 (1H, m), 7.00 (1H, dt, J6.9 Hz, 1.2 Hz).

Provenance & Evidence