Triphenylphosphine → Phosphonium, (4-methyl-3-pentenyl)triphenyl-, bromide

HRID 247435Notes

Reaction equation

HRID 247435 reaction equation
[Br:1][CH2:2][CH2:3][CH:4]=[C:5]([CH3:7])[CH3:6].[C:8]1([P:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(#N)C>[Br-:1].[CH3:6][C:5]([CH3:7])=[CH:4][CH2:3][CH2:2][P+:14]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 1375215-Bromo-2-methyl-2-pentene

Product 1

HCID 11304821Phosphonium, (4-methyl-3-pentenyl)triphenyl-, bromideYield 70.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 5-bromo-2-methyl-2-pentene (489.2 mg, 3 mmole) and triphenylphosphine (787 mg, 3 mmole) in 6 ml of acetonitrile was stirred at 95° C. (oil bath temperature) under nitrogen for 20 hours. The solvent was evaporated by a stream of nitrogen. The residue was dried in vacuo at room temperature to give a foam. This was rinsed with ethyl ether to give a white solid which was filtered, washed with ethyl ether and dried in vacuo at 100° C. for 4 hours to afford 905 mg of (4-methyl-3-pentenyl)triphenylphosphonium bromide.

Workup

  1. customThe solvent was evaporated by a stream of nitrogen
  2. customThe residue was dried in vacuo at room temperature
  3. customto give a foam
  4. washThis was rinsed with ethyl ether
  5. customto give a white solid which
  6. filtrationwas filtered
  7. washwashed with ethyl ether
  8. customdried in vacuo at 100° C. for 4 hours

Sources & evidence

ORD record
ord-e746320071194ca58ea97c8f7bc9d24d
Source dataset
uspto-grants-1987_11
Patent number
US04707494

Reaction notes

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