Phenylacetylene → 2,5-Diphenyl-1-benzofuran

HRID 1452727Notes

Reaction equation

[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17](I)[CH:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:1]1([C:7]2[O:21][C:18]3[CH:19]=[CH:20][C:15]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:16][C:17]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 10821Phenylacetylene

HCID 41061404-Hydroxy-3-iodobiphenyl

Product 1

HCID 142489342,5-Diphenyl-1-benzofuran

Procedure

The general procedure was used to convert phenylacetylene and 4-phenyl-2-iodophenol to the title product. Purification by flash chromatography (10% CH2Cl2 in hexanes as the eluent) gave the analytically pure product as a white solid (427 mg, 79% yield). 1H NMR (300 MHz, CDCl3) δ 7.88 (d, J=7.53, 2H), 7.78-7.75 (m, 1H), 7.67-7.33 (m, 10H), 7.07 (s, 1H). 13C NMR (75 MHz, CDCl3) δ 156.56, 154.49, 141.63, 136.61, 130.37, 129.74, 128.79, 128.73, 128.62, 127.41, 126.86, 124.93, 123.98, 119.36, 111.25, 101.45. Anal. Calcd. For C20H14O: C, 88.86; H, 5.22. Found C, 88.99; H, 5.28. m.p.: 166-167° C. (lit., 8166-168° C.).

Sources & evidence

ORD record: ord-1341a39ffbac48b6bce4c112ff0f7235
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473786B1

Reaction notes

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