Ethane → 1-Bromo-4-(1-propynyl)benzene
Reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][CH3:11].BrBr>>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1)#[C:10][CH3:11]Participants
4
Procedure
A solution of 1 g of 1-(1-propynyl)-4-bromo-benzene (produced from 4-bromobenzaldehyde by Wittig reaction, bromination of the resulting ethane and bromine elimination analogously to Example 1e) is reacted with 700 mg of tetrakis(triphenylphosphine)palladium (0) and 1.53 g of 4-(4-pentylphenyl)-2,3-difluoro-benzeneboric acid as described under a). Chromatography on silica gel with 3% ethyl acetate in petroleum ether and fractional crystallization from ethyl acetate gives 0.84 g of 1-(4-pentylphenyl)-2,3-difluoro-4-[4-(1-propynyl)-phenyl]benzene, m.p. 102.9° C.; cl.p. (N-I) 198.9° C.
Sources & evidence
- ORD record
- ord-5326648965514d7c8df40b3479e36b66
- Source dataset
- uspto-grants-1994_07
- Patent number
- US05328637
Reaction notes
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