Allyl Alcohol → 3-(3,4-Dichlorophenyl)propanal

Participants

Reaction Conditions

Reaction Steps

Palladium(II) acetate (0.17 g, 0.73 mmol) was added to a mixture of 1,2-dichloro-4-iodobenzene (2.00 g, 7.33 mmol), prop-2-en-1-ol (0.75 mL, 11 mmol), benzyltriethylammonium chloride (1.67 g, 7.33 mmol) and sodium bicarbonate (1.54 g, 18.3 mmol) in DMF (5 mL) and the mixture was degassed and back filled with Ar three times. The reaction mixture was heated at 60° C. for 2 h. The mixture was diluted with Et2O (15 mL) and H2O (15 mL) and the mixture was filtered through a celite pad. The organic layer was separated and the aqueous layer was extracted with E2O twice. The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by ISCO chromatography (EtOAc/Hexanes 0-10% over 20 min, column 80 g, flow rate 40 mL/min) to give Intermediate 16A (1.0 g, 4.9 mmol, 67% yield) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.78 (2H, t, J=7.3 Hz), 2.91 (2H, t, J=7.3 Hz), 7.03 (1H, dd, J=8.2, 2.1 Hz), 7.29 (1H, d, J=2.3 Hz), 7.35 (1H, d, J=8.0 Hz), 9.81 (1H, s).

Provenance & Evidence