2-Iodophenol → 2-(4-Vinyl-phenyl)-benzo[b]furan
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH2:10])=[CH:5][CH:4]=1)#[CH:2].I[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18]>>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:18][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH:10]=2)=[CH:5][CH:4]=1)=[CH2:2]Participants
3
Procedure
The general procedure was used to convert 1-Ethynyl-4-vinyl-benzene and 2-iodophenol to the title product. Purification by flash chromatography (hexanes as the eluent) gave the analytically pure product as a white solid (300 mg, 68% yield). 1H NMR (300 MHz, CDCl3) δ 7.79 (d, J=8.45, 2H), 7.56-7.44 (m, 4H), 7.29-7.19 (m, 2H), 6.98 (s, 1H), 6.74 (dd, J=10.93 and J=6.59, 1H), 5.78 (d, J=17.71, 1H), 5.28 (d, J=10.93, 1H). 13C NMR (75 MHz, CDCl3) δ 155.66, 154.87, 137.69, 136.26, 129.75, 129.22, 126.61, 125.02, 124.28, 122.94, 120.87, 114.40, 111.13, 101.37. Anal. Calcd. for C16H12O: C, 87.25; H, 5.49. Found C, 87.54; H, 5.62. m.p.: 164-165° C.
Sources & evidence
- ORD record
- ord-71c2bbbea578426c85cfc28e31af0b06
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473786B1
Reaction notes
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