Triphenylphosphine → [4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide
Reaction equation
[Br:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[CH:13]1[CH:18]=[CH:17][C:16]([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[Br-:1].[CH3:10][O:9][C:7]([C:6]1[CH:11]=[CH:12][C:3]([CH2:2][P+:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:16]2[CH:15]=[CH:14][CH:13]=[CH:18][CH:17]=2)=[CH:4][CH:5]=1)=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
A mixture of methyl 4-(bromomethyl)benzoate (5 g, 22 mmol) and PPh3 (5.77 g, 22 mmol) in 150 mL of toluene were stirred at 120° C. for 5 hours. The mixture was cooled to room temperature and filtered dried to give (4-(methoxycarbonyl)benzyl)triphenylphosphonium bromide (8.8 g, 82%) as a white solid 1H NMR (300 MHz, DMSO): δ 7.92-7.63 (m, 17H), 7.11-7.08 (m, 2H), 5.32-5.26 (m, 2H), 3.32 (s, 3H).
Workup
- temperatureThe mixture was cooled to room temperature
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-6c1320babfcf4d9181a4b0ea7365862e
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921383B2
Reaction notes
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