Acetonitrile → (4-Carboxy-4,4-difluorobutyl)(triphenyl)phosphanium bromide

HRID 569928Notes

Reaction equation

HRID 569928 reaction equation
C(#N)C.[C:4]1([P:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:23][CH2:24][CH2:25][CH2:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29]>C1(C)C=CC=CC=1>[Br-:23].[C:28]([C:27]([F:32])([F:31])[CH2:26][CH2:25][CH2:24][P+:10]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([OH:30])=[O:29]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 137699515-Bromo-2,2-difluoropentanoic acid

Product 1

HCID 20146459(4-Carboxy-4,4-difluorobutyl)(triphenyl)phosphanium bromideYield 96.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
5 °C

Procedure

Acetonitrile (23 ml) was added to a mixture of triphenylphosphine (6.7 g, 25.7 mmole) and Part (6) compound (4.6 g, 21.2 mmole). The solution was heated at gentle reflux under magnetic stirring for 30 hours. Toluene (46 ml) was then added and the reaction was brought to reflux for a brief period. The reaction was allowed to cool to 5° C. and kept overnight. The resulting white precipitates were collected, washed with cold acetonitrile/toluene (1/2), and dried in a heated vacuum oven (60° C.~5 mmHg) to give the title bromide (9.8 g, 20.4 mmole, 96.5%) as white solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureat gentle reflux
  3. temperatureto reflux for a brief period
  4. waitkept overnight
  5. customThe resulting white precipitates
  6. customwere collected
  7. washwashed with cold acetonitrile/toluene (1/2)
  8. customdried in a heated vacuum oven (60° C.~5 mmHg)

Sources & evidence

ORD record
ord-91203bff665b4ccaac8a33f9f18f443a
Source dataset
uspto-grants-1988_03
Patent number
US04734424

Reaction notes

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