Triphenylphosphine → (1-Methyl-(E)-2-pentenyl)triphenylphosphonium bromide

HRID 1085769Notes

Reaction equation

HRID 1085769 reaction equation
[C:1]1([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:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH:21](/[CH:23]=[CH:24]/[CH2:25][CH3:26])[CH3:22]>C(#N)C>[Br-:20].[CH3:22][CH:21]([P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)/[CH:23]=[CH:24]/[CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 11776Triphenylphosphine2×HCID 158813342-bromo-(E)-3-hexene2×

Product 1

HCID 20058850(1-Methyl-(E)-2-pentenyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound was prepared from triphenylphosphine and 2-bromo-(E)-3-hexene, a compound which was reported previously (Bianchini and Guillemonat, 1968). Triphenylphosphine (1.6 g, 0.0061 mole) and 2-bromo-(E)-3-hexene (1.0 g, 0.0061 mole) were added to 10 ml dry acetonitrile and refluxed for 6 hr. The solvent was removed by rotary evaporation. The thick, sticky liquid product was stirred with dry ether 4 times, with the ether being decanted. After removing further traces of ether by rotary evaporation, the product was placed in a vacuum desiccator for 6 hr, where the product became a friable white solid (1.6 g, 61%).

Workup

  1. temperaturerefluxed for 6 hr
  2. customThe solvent was removed by rotary evaporation
  3. customdecanted
  4. customAfter removing further traces of ether
  5. customby rotary evaporation

Sources & evidence

ORD record
ord-f332d3a5945d4d548336a4c4e45f7e3e
Source dataset
uspto-grants-1991_04
Patent number
US05011683

Reaction notes

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