Potassium Carbonate → 4-[1-(1,1,2,2,2-Pentafluoroethyl)-ethoxy]-benzonitrile

HRID 911635Notes

Reaction equation

HRID 911635 reaction equation
C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[F:16][C:17]([F:25])([C:21]([F:24])([F:23])[F:22])[CH:18]([OH:20])[CH3:19]>CN(C=O)C.CCCCCC.CCOC(C)=O>[F:16][C:17]([CH:18]([O:20][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)[CH3:19])([F:25])[C:21]([F:24])([F:23])[F:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 789913,3,4,4,4-Pentafluorobutan-2-ol

Product 1

HCID 576564594-[1-(1,1,2,2,2-Pentafluoroethyl)-ethoxy]-benzonitrileYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
130 °C

Procedure

Add potassium carbonate (27.4 g, 198 mmol) to a mixture of 4-fluorobenzonitrile (8 g, 66 mmol) and (±)-3,3,4,4,4-pentafluoro-2-butanol (17.2 g, 105 mmol) in anhydrous DMF (60 mL). Heat the mixture in a sealed flask for 4 h at 130° C. Cool the reaction to ambient temperature, dilute with hexane/EtOAc (1:1, 350 mL) and wash with aqueous 5% sodium chloride (3×100 mL). Collect the organic layer, dry over Na2SO4, filter and concentrate in vacuo to obtain the desired intermediate (17.1 g, 98%). GC-MS m/z: 432 (M+).

Workup

  1. temperatureCool
  2. customthe reaction to ambient temperature
  3. washwash with aqueous 5% sodium chloride (3×100 mL)
  4. customCollect the organic layer
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-dcc290c456b64bac8966ecfe37284b2f
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…