3-Buten-2-ol → 4-(3,4-Dichlorophenyl)butan-2-one

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with palladium acetate (0.165 g, 0.733 mmol), 1,2-dichloro-4-iodobenzene (2.00 g, 7.33 mmol), but-3-en-2-ol (0.793 g, 11.0 mmol), tetrabutylammonium chloride, hydrate (2.17 g, 7.33 mmol), and sodium bicarbonate (1.539 g, 18.32 mmol). DMF (5 mL) was added via syringe and the reaction mixture was degassed three times. The mixture was heated at 60° C. overnight. The reaction mixture was allowed to cool to rt, diluted with ether and the organic layer was washed with water. The organic layer was separated, dried with MgSO4, filtered and concentrated. The crude residue was purified by silica gel chromatography with an eluent of 10% ethyl acetate/hexanes to afford the desired product Intermediate 29A (1.40 g, 6.45 mmol, 88% yield). LC-MS (ESI) m/z 216.9 (M+H), RT=2.01 min (Method B).

Provenance & Evidence