Phenylacetylene → 5-Cyano-2-phenyl-benzo[b]furan
Reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13](I)[CH:12]=1)#[N:10]>>[C:9]([C:11]1[CH:16]=[CH:15][C:14]2[O:17][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][C:13]=2[CH:12]=1)#[N:10]Participants
3
Procedure
The general procedure was used to convert phenylacetylene and 4-cyano-2-iodophenol to the title product. Purification by flash chromatography (15% ethyl acetate in hexanes as the eluent) gave the analytically pure product as a white solid (421 mg, 96% yield). 1H NMR (300 MHz, CDCl3) δ 7.88-7.82 (m, 3H), 7.58-7.40 (m, 5H), 7.01 (s, 1H). 13C NMR (75 MHz, CDCl3) δ 158.30, 156.41, 129.85, 129.55, 129.23, 128.98, 127.84, 125.72, 125.22, 119.49, 112.25, 106.85, 100.72. Anal. Calcd. for C15H9NO: C, 82.18; H, 4.14; N, 6.39. Found C, 82.04; H, 4.21; N, 6.21. m.p.: 143-145° C.
Sources & evidence
- ORD record
- ord-50ac9c1ee8e24cb19f3542983beccc31
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473786B1
Reaction notes
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