Allyl Alcohol → 3-(2-Chlorophenyl)propanal

Participants

Reaction Conditions

Reaction Steps

2-Chloro-iodobenzene (700 mg), allyl alcohol (256 mg, 1.5 eq.), palladium acetate (13 mg, 0.02 eq), sodium bicarbonate (616 mg, 2.5 eq), and tetrabutylammonium chloride (816 mg, 1 eq) were mixed together in anhydrous DMF (12 mL). The mixture was stirred at 30° C. for 24 h, then diluted with water. The crude mixture was extracted into EtOAc 3×, and the organic layer was washed with water twice, then brine, and then dried over sodium sulfate, and concentrated. The residue was purified by chromatography (gradient: 88:12 hexanes:EtOAc to 1:1 hexanes:EtOAc) delivering the product (200 mg, 40% yield). 1H-NMR (300 MHz, CDCl3) δ 9.80 (s, 1H), 7.38-7.30 (m, 1H), 7.28-7.10 (m, 3H), 3.10-3.02 (m, 2H), 2.84-2.68 (m, 2H).

Provenance & Evidence