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

HRID 127744

Reaction equation

HRID 127744 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-35dab869babf469cba52a248837e4e90
Source dataset
uspto-grants-1981_03
Patent number
US04256878

Linked notes

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