Benzyl Bromide → (5-Bromopentyl)benzene

HRID 2237355Notes

Reaction equation

HRID 2237355 reaction equation
[Br-].[C:2]1([CH2:8][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:47]([Br:54])[C:48]1C=CC=[CH:50][CH:49]=1>C1(C)C=CC=CC=1>[Br:54][CH2:47][CH2:48][CH2:49][CH2:50][CH2:8][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11776TriphenylphosphineHCID 2734970Benzyltriphenylphosphonium bromide

Product 1

HCID 285561(5-Bromopentyl)benzeneYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phenylmethyl-triphenylphosphonium bromide (51 a) (PAA 59). Triphenylphosphine (2.364 g, 9.00 mmol) was added to benzyl bromide (1.348 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 24 h, then concentrated in vacuo. The resulting white amorphous solid was triturated with ether (3×20 mL) to yield 3.268 g (94%) white powder. 1H NMR (CDCl3, 300 MHz) δ 7.58-7.78 (m, 15H), 7.10-7.26 (m, 5H), 5.34-5.42 (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-ebc5ced329824d9190c1a8b4ab78847a
Source dataset
uspto-grants-2010_05
Patent number
US07718600B2

Reaction notes

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