Triphenylphosphine → (3,4,5-Tribromo-2-thenyl)triphenylphosphonium chloride

HRID 1764557Notes

Reaction equation

HRID 1764557 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.[Br:20][C:21]1[C:25]([Br:26])=[C:24]([Br:27])[S:23][C:22]=1[CH2:28][Cl:29]>C1(C)C=CC=CC=1>[Cl-:29].[Br:20][C:21]1[C:25]([Br:26])=[C:24]([Br:27])[S:23][C:22]=1[CH2:28][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 151249082,3,4-Tribromo-5-(chloromethyl)thiophene

Product 1

HCID 20285678(3,4,5-Tribromo-2-thenyl)triphenylphosphonium chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triphenylphosphine (9.0 g.) and 10.4 g. of 3,4,5-tribromo-2-chloromethylthiophene were dissolved in 200 ml. of toluene. The mixture was refluxed overnight under argon, cooled to room temperature and the precipitated phosphonium salt was collected by filtration, washed several times with cold benzene and dried at 80° C. under high vacuum. The resulting (3,4,5-tribromo-2-thenyl)triphenylphosphonium chloride has a m.p. 248°-249° C.

Workup

  1. temperatureThe mixture was refluxed overnight under argon
  2. filtrationthe precipitated 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-9a6bdb933960472a809bea85f566a257
Source dataset
uspto-grants-1978_09
Patent number
US04116975

Reaction notes

Loading…