Triphenylphosphine → Triphenyl[3-(3,4,5-trimethoxyphenyl)propyl]phosphonium bromide

HRID 1109659Notes

Reaction equation

HRID 1109659 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=1.[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[Br-:1].[C:30]1([P+:23]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:2][CH2:3][CH2:4][C:5]2[CH:6]=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 226096115-(3-Bromopropyl)-1,2,3-trimethoxybenzene

Product 1

HCID 19020969Triphenyl[3-(3,4,5-trimethoxyphenyl)propyl]phosphonium bromideYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dissolved in 50 ml of toluene were 7.65 g (26.5 mmol) of 5-(3-bromopropyl)-1,2,3-trimethoxybenzene and 6.9 g (26.5 mmol) of triphenylphosphine, followed by heating under reflux for 23 hours. The reaction mixture was allowed to cool down to room temperature. The supernatant was thereafter removed by decantation, whereby 7.46 g of crude triphenyl[3-(3,4,5-trimethoxyphenyl)propyl]phosphonium bromide were obtained as colorless oil (yield: 51%). The crude oil was used in the next reaction without purification.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 23 hours
  3. customThe supernatant was thereafter removed by decantation

Sources & evidence

ORD record
ord-8850c8388fe348f0bd51a5abf843c299
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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