Dibromomethane → Phosphonium, (bromomethyl)triphenyl-, bromide (1:1)

HRID 1441011Notes

Reaction equation

HRID 1441011 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][CH2:21][Br:22]>C1(C)C=CC=CC=1>[Br-:20].[Br:22][CH2:21][P+:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 3024DibromomethaneHCID 11776Triphenylphosphine

Product 1

HCID 2733422Phosphonium, (bromomethyl)triphenyl-, bromide (1:1)Yield 78.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, a stirred solution of 215.0 grams (0.82 mole) of triphenylphosphine and 115 mL (1.64 moles) of dibromomethane in 600 mL of toluene was heated at reflux for about eight hours. After this time a solid was collected by filtration. The filtrate was again heated to reflux where it stirred for an additional eight hours. The mixture was cooled and additional solid was collected by filtration. The two solids were combined, yielding about 280 grams of bromomethyl triphenylphosphonium bromide.

Workup

  1. temperatureat reflux for about eight hours
  2. filtrationAfter this time a solid was collected by filtration
  3. temperatureThe filtrate was again heated
  4. temperatureto reflux where it
  5. temperatureThe mixture was cooled
  6. filtrationadditional solid was collected by filtration

Sources & evidence

ORD record
ord-34f8864c9e95476a8fcb336880a1cafe
Source dataset
uspto-grants-1996_03
Patent number
US05502054

Reaction notes

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