Triphenylphosphine → (3-Methoxypropyl)triphenylphosphonium bromide

HRID 1809813Notes

Reaction equation

HRID 1809813 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[Br:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25]>C1(C)C=CC=CC=1>[Br-:20].[CH3:25][O:24][CH2:23][CH2:22][CH2:21][P+:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 5245511-Bromo-3-methoxypropane

Product 1

HCID 21458797(3-Methoxypropyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of PPh3 (42.8 g, 163.2 mmol) and 1-bromo-3-methoxypropane (25 g, 163.3 mmol) in toluene (70 mL) is heated at 150° C. in an autoclave for 44 h. After completion of the reaction, the mixture is filtered and the precipitate washed with toluene and dried under high vacuum for 4 h affording the title compound as a white powder. Rt (HPLC, Nucleosil C18, 10:90-100:0 CH3CN/H2O+0.1% TFA within 5 min, then 100% CH3CN+0.1% TFA): 5.06 min.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture is filtered
  3. washthe precipitate washed with toluene
  4. customdried under high vacuum for 4 h

Sources & evidence

ORD record
ord-7977bf6a22944ea8908f339d5b2c9a7a
Source dataset
uspto-grants-2013_01
Patent number
US08362040B2

Reaction notes

Loading…