Hydrogen Bromide → HCID 86613566, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(4-fluoro-phenyl)-5-methoxyrnethyl-isoxazole-4-carboxylic acid chloride (2.7 g, 10.0 mmol) in methylene chloride (50 mL) was added diazomethane solution in ether (0.1 N, 100 mL) at ice-bath cooling temperature. The reaction was stirred for 1.5 h at 0° C. and allowed to stand overnight in a freezer at 0° C. An aqueous solution of hydrobromic acid (>40 wt %, 70 mL) was added dropwise to the reaction solution at ice-bath cooling temperature. After complete addition, the resulting mixture was stirred at 0° C. for 0.5 h and then allowed to warm up to room temperature and stirred for 1.5 h. The organic layer was separated, and the aqueous phase was extracted with ether. The combined ether solution was then washed with water and brine, dried over sodium sulphate and evaporated to afford the crude title compound (3.8 g) which was obtained as a light yellow liquid. MS: m/e=328.0/330.4 [M+H]+.

Provenance & Evidence