Phenylacetylene → HCID 12023031, compound

HRID 1452728Notes

Reaction equation

HRID 1452728 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12](I)[CH:11]=1>>[Br: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 109245324-Bromo-2-iodophenol

Product 1

HCID 12023031HCID 12023031, compound

Procedure

The general procedure was used to convert phenylacetylene and 4-bromo-2-iodophenol to the title product. Purification by flash chromatography (20% CH2Cl2 in hexanes as the eluent) gave the analytically pure product as a white solid (468 mg, 86% yield). 1H NMR (300 MHz, CDCl3) δ 7.82 (d, J=6.97, 2H), 7.69-7.67 (m, 1H), 7.46-7.35 (m, 5H), 6.91 (s, 1H). 13C NMR (75 MHz, CDCl3) δ 157.18, 153.56, 131.17, 129.85, 128.97, 128.82, 127.04, 125.02, 123.43, 115.95, 112.56, 100.58. Anal. Calcd. for C14H9BrO: C, 61.57; H, 3.32; Br, 29.26. Found C, 61.46; H, 3.26; Br, 29.50. m.p.: 157° C. (lit.,9, 158-159° C.).

Sources & evidence

ORD record
ord-a500326362f6413ea7050123db41bd5b
Source dataset
uspto-grants-2009_01
Patent number
US07473786B1

Reaction notes

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