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

HRID 978048Notes

Reaction equation

HRID 978048 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][CH:25]=[CH: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 54242836HCID 54242836, compound

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-c72999dc05424b5f92c12004544e3936
Source dataset
uspto-grants-1987_05
Patent number
US04663336

Reaction notes

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