2-Iodophenol → HCID 11447426, compound

HRID 1452719Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10])#[CH:2].I[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18]>>[CH3:10][O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]1[O:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:2]=1

Participants

Reactant 2

HCID 107842-Iodophenol

HCID 5829121-Ethynyl-2-methoxybenzene

Product 1

HCID 11447426HCID 11447426, compound

Procedure

The general procedure was used to convert 2-ethynyl-anisole and 2-iodophenol to the title product. Purification by flash chromatography (10% ethyl acetate in hexanes as the eluent) gave the analytically pure product as a white solid (348 mg, 77% yield). 1H NMR (300 MHz, CDCl3) δ 8.05 (d, J=7.73, 1H), 7.58 (d, J=6.41, 1H), 7.48 (d, J=8.10, 1H), 7.34 (s, 1H), 7.26-7.18 (m, 3H), 7.03 (t, 1H), 6.89 (d, J=8.29, 1H), 3.86 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 156.42, 153.83, 152.15, 129.77, 129.20, 126.95, 124.08, 122.62, 121.01, 120.69, 119.25, 110.93, 110.78, 106.31, 55.87. Anal. Calcd. for C15H12O2: C, 80.34; H, 5.39. Found C, 80.60; H, 5.65. m.p.: 76° C.

Sources & evidence

ORD record: ord-9a15092f4a9843c29a28195fba71ccf8
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473786B1

Reaction notes

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