Benzene, 1-bromo-4-ethynyl- → HCID 76556509, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13](=[O:17])/[CH:14]=[CH:15]\I)[CH3:11]>>[CH2:10]([O:12][C:13](=[O:17])[CH:14]=[CH:15][C:9]#[C:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:11]Participants
3
Procedure
The general procedure was used to convert 1-Bromo-4-ethynyl-benzene and (Z)-ethyl-3-iodoacrylate to the title product in 20 hours. Purification by flash chromatography (355 mg, 20% ethyl acetate in hexane as the eluent) gave the analytically pure product as a light yellow oil (65% yield). 1H NMR (400 MHz, CDCl3) δ 7.48-7.46 (d, J=8.5, 2H), 7.39-7.36 (d, J=8.5, 2H), 6.33-6.30 (d, J=11.4, 1H), 6.16-6.13 (d, J=11.4, 1H), 4.27-4.22 (q, J=7.1, 2H), 1.33-1.29 (t, J=7.1, 3H). 13C NMR (100 MHz, CDCl3) δ 164.64, 133.40, 131.68, 128.69, 123.61, 122.49, 121.60, 99.81, 87.38, 60.46, 14.29. Anal. Calcd. for C13H11BrO2: C, 55.94; H, 3.97; Br, 28.63; Found C, 56.05; H, 4.07; Br, 27.6.
Sources & evidence
- ORD record
- ord-e15debac33c047a19f63f2a18c3be40e
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473797B2
Reaction notes
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