2-Iodophenol → 2-(2-(Methoxycarbonyl)phenyl)benzo[b]furan
Reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[CH:11].I[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20]>>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:20][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH:11]=1)=[O:12]Participants
3
Procedure
The general procedure was used to convert 2-Ethynyl-benzoic acid methyl ester and 2-iodophenol to the title product. Purification by flash chromatography (10% ethyl acetate in hexanes) gave the analytically pure product as an oil (458 mg, 67% yield). 1H NMR δ 7.75-7.70 (m, 2H), 7.61-7.40 (m, 4H), 7.31-7.22 (m, 2H), 6.92 (s, 1H), 3.81 (s, 3H). 3C NMR δ 169.35, 155.10, 154.67, 131.09, 130.94, 129.61, 129.36, 128.99, 128.88, 128.64, 124.54, 122.94, 121.21, 111.09, 104.38, 52.48. Anal. Calcd. for C16H12O3: C, 76.18; H, 4.79. Found C, 75.95; H, 4.75.
Sources & evidence
- ORD record
- ord-3bc42a33e22d4c519cdf7aaba4461e41
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473786B1
Reaction notes
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