Triphenylphosphine → 2-{3-[3-(4-Fluorophenoxy)propoxy]phenyl}-ethyl triphenylphosphonium bromide
Reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH2:17][CH2:18][Br:19])[CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1.[C:22]1([P:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C>[Br-:19].[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH2:17][CH2:18][P+:28]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1Participants
4
Procedure
A solution of 20 mmol of bromide (example 141) and 30 mmol of triphenyl phosphine in 60 ml of ethanol was refluxed 20 hours under nitrogen and then cooled and evaporated in vacuo. The residue was chromatographed on silica gel using first CHCl3 to elute starting material residues and then 5% CH3OH in CHCl3 to elute the product. Evaporation of pure fractions yielded the title compound as a viscous oil.