Carbon tetrabromide → HCID 67502077, compound

Participants

Reaction Steps

To a solution of alcohol 30a (35 mg, 0.12 mmol) in dichloromethane (4 mL) at 0° C. were added potassium carbonate (71 mg, 0.51 mmol), triphenylphosphine (88 mg, 0.34 mmol), and carbon tetrabromide (112 mg, 0.35 mmol). The solution was allowed to return at room temperature and was stirred for 90 min. The resulting solution was diluted with dichloromethane (25 mL), washed with a 10% sodium bicarbonate solution and filtered over a cotton plug. Purification of the resulting crude product by flash chromatography using ethyl acetate/hexane (7:3) as an eluant gave the desired compound 31a (22 mg, 60%). 1H NMR (400 MHz, Acetone-d6) δ: 2.71 (t, 4H, J=5.12 Hz), 2.82 (m, 2H), 3.56 (m, 6H), 7.27 (dd, 1H, J1=6.23 Hz, J2=2.61 Hz), 7.35 (d, 1H, J=2.53 Hz), 7.78 (d, 1H, J=8.84 Hz).

Provenance & Evidence