2-Iodophenol → 2-Phenyl-benzofuran

HRID 1452716Notes

Reaction equation

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

Participants

Reactant 2

HCID 107842-Iodophenol

HCID 10821Phenylacetylene

Product 1

HCID 35179362-Phenyl-benzofuran

Procedure

The general procedure was used to convert phenylacetylene and 2-iodophenol to the title product. Purification by flash chromatography (hexanes as the eluent) gave the analytically pure product as a white solid (358 mg, 93% yield). 1H NMR (300 MHz, CDCl3) δ 7.86-7.83 (dd, J=6.97, 2H) 7.56-7.49 (m, 2H), 7.41-7.39 (m, 2H), 7.34-7.18 (m, 3H), 6.97 (s, 1H). 13C NMR (75 MHz, CDCl3) δ 155.88, 154.86, 130.44, 129.20, 128.75, 128.51, 124.89, 124.24, 122.91, 120.89, 111.16, 101.28. Anal. Calcd. for C14H10O: C, 86.57; H, 5.19. Found C, 86.41; H, 5.34. m.p.: 120° C. (lit., 3118-120° C.).

Sources & evidence

ORD record: ord-8df5cb600b304ed28c5a1e0334a7783e
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473786B1

Reaction notes

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