Triphenylphosphine → (2,5-Dimethyl-3-thenyl)triphenylphosphonium chloride

HRID 460953

Reaction equation

HRID 460953 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.[CH3:20][C:21]1[S:22][C:23]([CH3:28])=[CH:24][C:25]=1[CH2:26][Cl:27]>C1(C)C=CC=CC=1>[Cl-:27].[CH3:20][C:21]1[S:22][C:23]([CH3:28])=[CH:24][C:25]=1[CH2:26][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 128752613-(Chloromethyl)-2,5-dimethylthiophene

Product 1

HCID 20285688(2,5-Dimethyl-3-thenyl)triphenylphosphonium chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triphenylphosphine (11.8 g.) and 7.0 g. of 2,5-dimethyl-3-chloromethylthiophene were dissolved in 100 ml. of toluene. The mixture was refluxed overnight under argon, cooled to room temperature and the precipitated white phosphonium salt was collected by filtration, washed several times with cold benzene and dried at 80° C. under high vacuum. The resulting (2,5-dimethyl-3-thenyl)-triphenylphosphonium chloride has a m.p. 246°-250° C.

Workup

  1. temperatureThe mixture was refluxed overnight under argon
  2. filtrationthe precipitated white phosphonium salt was collected by filtration
  3. washwashed several times with cold benzene
  4. customdried at 80° C. under high vacuum

Sources & evidence

ORD record
ord-77bac11b374d4b569275e985baa2db7f
Source dataset
uspto-grants-1977_12
Patent number
US04061656

Linked notes

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