Potassium tert-butoxide → HCID 90389418, compound

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Reaction Steps

Potassium t-butoxide (176 mg, 1.572 mmol, Aldrich) was added in small portions over a time period of 20 min to a solution of 3-(5-bromo-2-fluorophenyl)-5-(chloromethyl)-4,5-dihydroisoxazole (200 mg, 0.684 mmol, 1d rac) in DMSO (4 mL) cooled with a water bath. After completed, the reaction was quenched by the addition of ice. EtOAc was added and the organic phase was separated. The organic phase was dried over MgSO4 and the solvent was removed under reduced pressure. The crude material was absorbed onto a plug of silica gel and purified by chromatography, eluting with 3% to 5% EtOAc in hexane, to provide the title compound as a colorless oil (154 mg, 0.601 mmol, 88% yield). MS m/z=257.9 [M+H]+. Calculated for C10H7BrFNO: 256.07.

Provenance & Evidence