Carbon tetrabromide → HCID 12147022, compound

Participants

Reaction Steps

A solution of triphenylphosphine (0.46 g, 1.75 mmol) in DMF (5 mL) was added to a mixture of 1-5 (0.49 g, 1.46 mmol) and carbon tetrabromide (0.68 g, 2.05 mmol) in DMF (5 mL) at 0° C. The resulting mixture was allowed to warm to room temperature and allowed to stir for 12 hours. The mixture was then concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography using ethyl acetate and hexane (3:1 to 2:1 gradient) as eluants to afford the title compound 1-6 (0.38 g, 66% yield) as a yellow solid. MS (m/e): 399. TLC: Rf (0.35) (EA/Hex); 1H NMR (400 MHz, CDCl3): δ 2.23 (m, 2H), 2.4 (s, 3H), 3.5 (t, 2H), 4.2 (t, 2H), 4.3 (s, 2H), 6.0 (d, 1H), 7.2(d, 1H), 7.3(m, 5H).

Provenance & Evidence