(3-Bromopropyl)benzene → HCID 24995449, compound
Reaction equation
[C:1]([C:4]1[C:5]([OH:13])=[CH:6][C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2].Br[CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:1]([C:4]1[C:5]([O:13][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:6][C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2]Participants
3
Procedure
5-Acetyl-6-hydroxybenzofuran (60 mg, 0.34 mmol) and 1-bromo-3-phenylpropane were reacted according to General Procedure A. The crude residue was purified by flash chromatography, eluting with diethyl ether:petroleum ether (1:9) to afford the title compound as a white solid (81 mg, 81%). 1H NMR (300 MHz, CDCl3): δ 2.26-2.16 (m, 2H), 2.69 (s, 3H), 2.85 (t, J=7.3 Hz, 2H), 4.07 (t, J=6.3 Hz, 2H), 6.72 (d, J=1.7 Hz, 1H), 6.99 (s, 1H), 7.32-7.19 (m, 5H), 7.54 (d, J=2.2 Hz, 1H), 7.99 (s, 1H). MS (ES+) m/z 294.9 (M+H+).
Workup
- customThe crude residue was purified by flash chromatography
- washeluting with diethyl ether:petroleum ether (1:9)