Triphenylphosphine → (4-Cyanobenzyl)triphenylphosphonium chloride

HRID 597544Notes

Reaction equation

HRID 597544 reaction equation
[PH4+].[C:2]1([P:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:21][CH2:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[Cl-:21].[C:27]([C:26]1[CH:29]=[CH:30][C:23]([CH2:22][P+:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:24][CH:25]=1)#[N:28]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 701274-(Chloromethyl)benzonitrileHCID 5460504Phosphonium

Product 1

HCID 2724468(4-Cyanobenzyl)triphenylphosphonium chlorideYield 57.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The phosphonium salt used for this preparation was made as follows:- a solution of triphenylphosphine (39.3g) and 4-chloromethylbenzonitrile (22.7g) in toluene (400 ml) was heated under reflux for 53 hr. After cooling, the solid was collected, washed with toluene and dried to give 4-cyanobenzyltriphenylphosphonium chloride (35.4g), νmax (nujol) 2230 (CN) and 1436 cm.-1 (PPH3), τ (d6 -DMSO; 60 MHz) values include 2.0-2.5 (aromatic protons), 4.47 (CH2).

Workup

  1. temperatureunder reflux for 53 hr
  2. temperatureAfter cooling
  3. customthe solid was collected
  4. washwashed with toluene
  5. customdried

Sources & evidence

ORD record
ord-ed1c973771ed4d2da23ec1d8e5663160
Source dataset
uspto-grants-1977_03
Patent number
US04014869

Reaction notes

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