Bromine → HCID 178422393, compound

Participants

Reaction Conditions

Reaction Steps

A 25 ml high-pressure tube equipped with a stir bar and a screw-on Teflon cap was charged with 6-methyl-benzo[d]isoxazol-3-ol (745 mg, 5.0 mmole, 1.0 eq) and glacial acetic acid (5.0 ml). Neat Br2 (774 μL, 15.0 mmoles, 3.0 eq) was added dropwise. After stirring at 80° C. for 20 hours, the reaction was allowed to cool slowly to room temperature. The resulting precipitate was collected by filtration and washed quickly with 3×1.0 ml of glacial acetic acid. Crystallization of this crude product (624 mg) from 50 ml of MeCN yielded 567 mg of the title compound (96% purity determined RP-HPLC). Additional crystallization from 70 ml of toluene provided 519 mg (46%) as a white solid (98.1% purity determined by HPLC). (1H DMSO-d6, 400 MHz) δ 12.45 (s, 1H), 7.94 (s, 1H), 7.61 (s, 1H), 2.45 (s, 3H); (13C CD3OD, 100 MHz) δ 165.96, 164.50, 142.34, 125.39, 119.73, 115.78, 112.67, 24.10.

Provenance & Evidence