Triphenylphosphine → 5-Carboxy-5,5-dimethylpentyltriphenylphosphonium bromide
Reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([CH3:11])([CH3:10])[C:7]([OH:9])=[O:8].[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(#N)C>[Br-:1].[C:7]([C:6]([CH3:11])([CH3:10])[CH2:5][CH2:4][CH2:3][CH2:2][P+:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([OH:9])=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
6-Bromo-2,2-dimethylhexanoic acid (3.8 g, 17 mmole) and triphenylphosphine (4.9 g, 18.7 mmole) were dissolved in acetonitrile (30 ml), and the solution was heated under reflux for 20 hours. After the completion of the reaction, the solvent was removed under reduced pressure, and the residue was treated with toluene, followed by thorough stirring. The insolubles were seperated from the toluene solution, and crystallized from ethyl acetate to give 5-carboxy-5,5-dimethylpentyltriphenylphosphonium bromide (4.8 g, 58%) [NMR (δ value): 1.10 (6H,s), 1.4-1.6 (6H), 3.4-3.8 (2H)].