Triphenylphosphine → (Cyclohexylmethyl)triphenylphosphonium bromide

HRID 982032Notes

Reaction equation

HRID 982032 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.[CH:20]1([CH2:26][Br:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C1(C)C=CC=CC=1>[Br-:27].[CH:20]1([CH2:26][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)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 20068889(Cyclohexylmethyl)triphenylphosphonium bromideYield 72.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5.80 g (21.9 mmol) of triphenylphosphine and 8.00 g (43.8 mmol) of cyclohexylmethyl bromide in 30 ml of toluene was heated at reflux for 4 days. After removal of solvent in vacuo, the residue was taken up in tetrahydrofuran and filtered to give 6.96 g (37%) of the desired compound.

Workup

  1. temperatureat reflux for 4 days
  2. customAfter removal of solvent in vacuo
  3. filtrationfiltered

Sources & evidence

ORD record
ord-75f38a57250745a583a27478752f273f
Source dataset
uspto-grants-1991_02
Patent number
US04994477

Reaction notes

Loading…