2-Iodophenol → HCID 10634549, compound

HRID 1452722Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[CH:6][CH:5]=1.I[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20]>>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:20][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH:11]=2)=[CH:6][CH:5]=1)=[O:12]

Participants

Reactant 2

HCID 107842-Iodophenol

HCID 640163Methyl 4-ethynylbenzoate

Product 1

HCID 10634549HCID 10634549, compound

Procedure

The general procedure was used to convert 4-Ethynyl-benzoic acid methyl ester and 2-iodophenol to the title product. Purification by flash chromatography (10% ethyl acetate in hexanes) gave the analytically pure product as a white solid (300 mg, 67% yield). 1H NMR δ 8.09 (dd, J=8.70, 2H), 7.90 (d, J=8.70, 2H), 7.52-7.62 (dd, J=8.10, 2H), 7.24-7.33 (m, 2H), 7.13 (s, 1H), 3.93 (s, 3H). 13C NMR δ 167.00, 155.50, 155.00, 134.80, 130.50, 130.00, 129.30, 125.40, 125.0, 123.60, 121.60, 111.70, 103.80, 52.60. Anal. Calcd. for C16H12O3: C, 76.18; H, 4.79. Found C, 75.97; H, 4.75. m.p. 176-178° C. (lit., 5176-177° C.).

Sources & evidence

ORD record: ord-4cb732417537400884c81aa7541ffd52
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473786B1

Reaction notes

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