Triphenylphosphine → (Diphenylmethyl)(triphenyl)phosphanium bromide

HRID 274195Notes

Reaction equation

HRID 274195 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]([Br:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C.C(OCC)C>[Br-:14].[C:28]1([P+:21]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 236603Bromodiphenylmethane

Product 1

HCID 522488(Diphenylmethyl)(triphenyl)phosphanium bromide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

6.2 parts of α-bromodiphenylmethane was dissolved in 100 parts of acetonitrile and 6.6 parts of triphenylphosphine was added thereto. The mixture was heated under reflux for 3 hr. The mixture was allowed to stand for cooling and then diluted with a small amount of diethyl ether. The resulting colorless crystals were collected by filtration and washed with a small amount of acetonitrile to obtain 10.5 parts of triphenyl (diphenylmethyl)phosphonium bromide (compound No. 66).

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 3 hr
  4. temperaturefor cooling
  5. filtrationThe resulting colorless crystals were collected by filtration
  6. washwashed with a small amount of acetonitrile

Sources & evidence

ORD record
ord-446cab35e1f04436a1da3badc1ef8062
Source dataset
uspto-grants-1995_02
Patent number
US05389486

Reaction notes

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