Phenylacetylene → 13141-45-2

HRID 1452815Notes

Reaction equation

HRID 1452815 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:1]1([C:7]#[C:8]/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 10821PhenylacetyleneHCID 615407HCID 615407, compound

Product 1

HCID 155151213141-45-2

Procedure

The modified procedure was used to convert phenyl acetylene and β-iodostyrene to the title product. Purification by flash chromatography (20% CH2Cl2 in hexanes) gave the analytically pure product as a light yellow solid (399 mg, 98% yield). 1H NMR (400 MHz, CDCl3) δ 7.47 (m, 2H), 7.43 (d, J=7.22, 2H), 7.4-7.27 (m, 6H), 7.03 (d, J=16.24, 1H), 6.37 (d, J=16.24). 13C NMR (100 MHz, CDCl3) δ 141.24, 136.31, 131.50, 128.71, 128.60, 128.32, 128.16, 126.29, 123.42, 108.13, 91.75, 88.91. Anal. Calcd. for C16H12: C, 94.08; H, 5.92; Found C, 93.96; H, 6.10. m.p.: 97-98° C. (lit: 96-97° C.)

Sources & evidence

ORD record
ord-80e0f6b0676e444eaed160211a7477fc
Source dataset
uspto-grants-2009_01
Patent number
US07473797B2

Reaction notes

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