4-Iodo-3,5-dimethyl-1,2-oxazole → 4-m-Bromophenyl-3,5-dimethylisoxazole

Participants

Reaction Steps

The reaction of 3,5-dimethyl-4-iodoisoxazole (Kochetkov, N. K. Zhurnal Obschchie Khimii, 31, 2167-2172 (1961)) (2.4 g, 11 mmol) with 3-bromophenylboronic acid (2.24 g, 11 mmol) using the procedure for the preparation of 3-(3'-bromophenyl)pyridine gave 3.3 g crude 4-m-bromophenyl-3,5-dimethylisoxazole. After a quick filtration on Si gel (eluting with CH2Cl2), the material was further purified by preparative TLC on 12-1000μ Si Gel GF plates (eluting with 10% acetone/hexane and extracting with 10% MeOH/CH2Cl2), to provide 1.2 g of the arylated isoxazole. Sublimation (ambient to 70° C., high vacuum) of 0.5 g provided 404 mg of analytically pure material.

Provenance & Evidence