2-Iodophenol → 2-(p-Tolyl)benzofuran

HRID 1452717Notes

Reaction equation

HRID 1452717 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1)#[CH:2].I[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17]>>[C:6]1([CH3:9])[CH:7]=[CH:8][C:3]([C:1]2[O:17][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH:2]=2)=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 107842-IodophenolHCID 13018p-Ethynyltoluene

Product 1

HCID 6384582-(p-Tolyl)benzofuran

Procedure

The general procedure was used to convert 4-ethynyl-toluene and 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 (268 mg, 64% yield). 1H NMR (300 MHz, CDCl3) δ 7.74 (d, J=8.29, 2H), 7.56-7.48 (m, 2H), 7.28-7.17 (m, 4H), 6.93 (s, 1H), 2.37 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 156.16, 154.75, 138.56, 132.85, 129.47, 127.73, 124.86, 123.97, 122.84, 120.72, 111.07, 100.54, 21.36 Anal. Calcd. for C15H12O: C, 86.51; H, 5.81. Found C, 86.34; H, 5.98. m.p.: 124-125° C. (lit., 3126-128° C.).

Sources & evidence

ORD record
ord-9e220bb5f25043b19eb3c25e3ae4f8ac
Source dataset
uspto-grants-2009_01
Patent number
US07473786B1

Reaction notes

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