Acetic Acid → 3-Bromo-5-(3-pyridylmethyl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A 1.3M solution of s-butyllithium in hexane (27.7 ml) was added dropwise to a stirred suspension of 3-(3,5-dibromobenzyl)pyridine (Preparation 3; 9.81 g) in dry ether (300 ml) at -78° C. under an atmosphere of dry nitrogen. The resulting mixture was stirred at -78° C. for 15 minutes and then N,N-dimethylformamide (6.60 g) was added dropwise. This mixture was stirred at -78° C. for a further 30 minutes, allowed to warm to -20° C. and the glacial acetic acid (12 ml) was added. After 10 minutes, water (150 ml) was added and the organic phase separated. The aqueous layer was washed with ethyl acetate, then the combined organic solutions washed with saturated aqueous sodium bicarbonate solution and dried (MgSO4). Evaporation under vacuum of the solvent gave a solid which was crystallised from ether-hexane to give the title compound (5.25 g), m.p. 97°-98° C. Found: C,56.21; H,3.71; N,5.19. C13H10BrNO requires C,56.54; H,3.65; N,5.07%.

Provenance & Evidence