(3-Bromopropyl)benzene → HCID 24995449, compound

HRID 1875362Notes

Reaction equation

HRID 1875362 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

Reactant 2

HCID 12503(3-Bromopropyl)benzeneHCID 114352451-(6-hydroxybenzofuran-5-yl)ethanone

Product 1

HCID 24995449HCID 24995449, compoundYield 81%

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

  1. customThe crude residue was purified by flash chromatography
  2. washeluting with diethyl ether:petroleum ether (1:9)

Sources & evidence

ORD record
ord-4b2c49c313814149b19491cc80f09c59
Source dataset
uspto-grants-2012_11
Patent number
US08309545B2

Reaction notes

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