Phenylacetylene → 5-Chloro-2-phenylbenzofuran

HRID 1452729Notes

Reaction equation

HRID 1452729 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12](I)[CH:11]=1>>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]2[O:16][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][C:12]=2[CH:11]=1

Participants

3

Reactant 2

HCID 10821PhenylacetyleneHCID 6202344-Chloro-2-iodophenol

Product 1

HCID 6150425-Chloro-2-phenylbenzofuran

Procedure

The general procedure was used to convert phenylacetylene and 4-chloro-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 (411 mg, 90% yield). 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=6.97, 2H), 7.52 (d, J=2.26, 1H), 7.46-7.35 (m, 4H), 7.21 (dd, J=6.59, 1H), 6.93 (s, 1H). 13C NMR (75 MHz, CDCl3) δ 157.36, 153.22, 130.56, 129.93, 128.98, 128.84, 128.46, 125.03, 124.37, 120.40, 112.10, 100.78. Anal. Calcd. for C14H9ClO: C, 73.53; H, 3.97; Cl, 15.50. Found C, 73.31; H, 3.99; Cl, 15.68. m.p.: 155.5-157° C. (lit., 10156° C.).

Sources & evidence

ORD record
ord-d7fde8c2296941aaa71275442b89f6aa
Source dataset
uspto-grants-2009_01
Patent number
US07473786B1

Reaction notes

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