Methanol → (E)-Methyl 2-(methoxyimino)-2-[2-(bromomethyl)phenyl]acetate

Participants

Reaction Steps

To a solution of isochroman-3,4-dione 4-(O-methyl-oxime) (5.6 g, 0.028 mol) in methanol (27 g) was added dropwise at 10-20° C. thionyl bromide (45.4 g, 0.22 mol) over a period of 1 h and the resulting mixture was stirred at ambient temperature overnight. The reaction was monitored by HPLC. Concentration of the mixture in vacuo led to a crude residue (14.2 g). A small amount of the residue (3.2 g) was purified by silica column chromatography to yield (2-bromomethyl-phenyl)-[(E)-methoxyimino]-acetic acid methyl ester as a colorless solid (0.8 g).

Provenance & Evidence