Triphenylphosphine → 3-Phenylpropyl triphenylphosphonium bromide

HRID 2237357Notes

Reaction equation

HRID 2237357 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][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[Br-:20].[C:24]1([CH2:23][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:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 12503(3-Bromopropyl)benzene

Product 1

HCID 109286473-Phenylpropyl triphenylphosphonium bromideYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triphenylphosphine (2.364 g, 9.00 mmol) was added to (3-bromo-propyl)-benzene (1.552 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. The resulting white amorphous solid was triturated with ether (3×20 mL) to yield 1.984 g (55%) white solid. 1H NMR (CDCl3, 300 MHz) δ7.66-7.83 (m, 15H), 7.19-7.27 (m, 5H), 3.92-4.02 (m, 2H), 3.06 (t, J=7.2 Hz, 2H), 1.92-2.00 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under argon
  3. concentrationconcentrated in vacuo
  4. customThe resulting white amorphous solid was triturated with ether (3×20 mL)

Sources & evidence

ORD record
ord-3269a267c4b44282811c468801b8c68a
Source dataset
uspto-grants-2010_05
Patent number
US07718600B2

Reaction notes

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