Triphenylphosphine → (Cyclohexylmethyl)triphenylphosphonium bromide

HRID 2103619Notes

Reaction equation

HRID 2103619 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][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C1(C)C=CC=CC=1>[Br-:20].[CH:22]1([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)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 20068889(Cyclohexylmethyl)triphenylphosphonium bromideYield 99.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
165 °C

Procedure

Mix triphenylphosphine (200 g, 0.76 mol) and bromomethyl-cyclohexane (400 g, 2.26 mol) under an argon atmosphere and stir 16 h at 165° C. Pour the reaction mixture into 750 mL toluene and stir until the suspension reached ambient temperature. Filter and wash the product with diethylether and dry under vaccum to get 332.3 g pure product. MS (m/e): 359.0 (M+H).

Workup

  1. stirringstir until the suspension
  2. customreached ambient temperature
  3. filtrationFilter
  4. washwash the product with diethylether
  5. customdry under vaccum

Sources & evidence

ORD record
ord-60f749e1b34d4df6ad6f5f37aaa32266
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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