Phenethyl bromide → Phenethyltriphenylphosphonium bromide

HRID 2237356Notes

Reaction equation

HRID 2237356 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][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[Br-:20].[C:23]1([CH2:22][CH2:21][P+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7666Phenethyl bromideHCID 11776Triphenylphosphine

Product 1

HCID 10863251Phenethyltriphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triphenylphosphine (2.364 g, 9.00 mmol) was added to (2-bromo-ethyl)-benzene (1.496 g, 8.00 mmol) in 35 mL toluene in a 100-mL round-bottom flask. The mixture was heated to reflux under argon and stirred 48 h, then concentrated in vacuo to a thick yellow oil. The oil was dissolved in boiling EtOH under argon. Benzene was added until an oil separated from the solution. The solution was heated under vacuum to remove all solvent and yield 3.6 g (100%) white foam. 1H NMR (CDCl3, 300 MHz) δ 7.67-7.91 (m, 15H), 7.17-7.32 (m, 5H), 4.25 (dt, J=12.6, 7.8 Hz, 2H), 3.08 (dt, J=12.9, 7.8 Hz, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under argon
  3. concentrationconcentrated in vacuo to a thick yellow oil
  4. dissolutionThe oil was dissolved
  5. additionBenzene was added until an oil
  6. customseparated from the solution
  7. temperatureThe solution was heated under vacuum
  8. customto remove all solvent and yield 3.6 g (100%) white foam

Sources & evidence

ORD record
ord-5fed652eaab4423eb6e4a1c1db96bb8f
Source dataset
uspto-grants-2010_05
Patent number
US07718600B2

Reaction notes

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