Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → 8-BROMO-2H-1-BENZOPYRAN-2-ONE

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-2-hydroxybenzaldehyde (402 mg, 2.0 mmol) in NMP (5 mL) was added carbethoxymethylene triphenylphosphorane (765 mg, 2.2 mmol). The reaction was heated at 210° C. for 3 h, then was cooled to RT and partitioned between water and ethyl acetate. The layers were separated and the organic layer was dried over MgSO4. Purification by flash chromatography on silica gel (2:1 hexanes/ethyl acetate) yielded the title compound (116 mg, 26%) as a light beige solid: MS (ES) m/e 227.0 (M+H)+.

Provenance & Evidence