Ethanol → (E)-2-(3-bromo-alpha-t-butoxyimino-4-fluorobenzyl)-3-hydroxypyridine

Participants

Reaction Steps

A mixture of 2-(3-bromo-4-fluorobenzoyl)-3-hydroxypyridine (1.26 g), O-t-butylhydroxylamine hydrochloride (1.08 g) and ethanol (10 mL) was refluxed for 2 hours. The reaction mixture was poured into water, and subjected to extraction with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, successively, and dried (sodium sulfate), followed by evaporating the solvent under reduced pressure. The residue was subjected to purification by means of a silica gel column (ethyl acetate--hexane) to afford (E)-2-(3-bromo-α-t-butoxyimino-4-fluorobenzyl)-3-hydroxypyridine (0.89 g) and (Z)-2-(3-bromo-α-t-butoxyimino-4-fluorobenzyl)-3-hydroxypyridine (0.51 g) (compounds 17 and 16).

Provenance & Evidence