1,5-Dibromopentane → HCID 11131348, compound

Participants

Reaction Steps

To a solution of methyl vanillate (9.109 g, 50 mmol) in acetone (200 mL) were added K2CO3 (27.64 g, 200 mmol) and 1,5-dibromopentane (20.4 mL, 150 mmol). The resulting mixture was heated to reflux. After 6 h, TLC showed no starting material left. The mixture was cooled to rt, and the solid was removed by filtration. The filtrate was concentrated. Purification by flash chromatography (silica gel, 8:2 hexanes/EtOAc) afforded 4-(5-bromopentyloxy)-3-methoxy-benzoic acid methyl ester 15 as white solid (13.65 g, 82%): 1HNMR (300 MHz, CDCl3) δ 1.60-1.66 (m, 2H), 1.85-1.97 (m, 4H), 3.42 (t, J=5.0 Hz, 2H), 3.87 (s, 3H), 3.89 (s, 3H), 4.06 (t, J=5.0 Hz, 2H), 6.85 (d, J=6.3 Hz, 1H), 7.52 (d, J=1.5 Hz, 1H), 7.63 (dd, J=6.3, 1.5 Hz, 1H); EIMS m/z 353 and 355 ([M]++Na).

Provenance & Evidence