Methyl formate → 3,5-Dichloro-4-pyridinecarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (1.6M in hexanes, 9.3 ml, 14.9 mmol) was added dropwise at 0° C. to a solution of diisopropylamine (1.95 ml, 14.9 mmol) in THF (30 ml). After 15 min. at 0° C., the solution was cooled to −78° C. and 3,5-dichloropyridine (2.0 g, 13.5 mmol) was added. After 1 h, methyl formate (0.92 ml) was added and the mixture warmed to room temperature over 2 h, diluted with 1N hydrochloric acid and extracted twice with ethyl acetate. The extracts were washed with brine, dried over sodium sulphate and evaporated to give a yellow oil which solidified, m.p. 110-111° C.

Provenance & Evidence