Acetone → HCID 18543379, compound

HRID 844322Notes

Reaction equation

HRID 844322 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[OH:12].CC(C)=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]#[N:26]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:10])([F:11])[F:9])=[CH:4][C:3]=1[O:12][CH2:24][C:25]#[N:26]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 5188882-Fluoro-5-(trifluoromethyl)phenol

Product 1

HCID 18543379HCID 18543379, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-fluoro-5-trifluoromethylphenol (25 g) in reagent grade acetone (0.55 L) is treated with solid potassium carbonate (7.7 g) followed by the rapid addition of neat bromoacetonitrile (10 mL). The heterogenous mixture is stirred vigorously for approximately 20 hours whereupon it is poured into water and extracted into diethyl ether. The combined ether extracts are washed with saturated sodium chloride and dried over anhydrous potassium carbonate. Filtration and concentration under reduced pressure gives a pale orange solid which is then chromatographed on silica gel, eluting with dichloromethane, to give the desired product as white solid (28.3 g).

Workup

  1. extractionextracted into diethyl ether
  2. washThe combined ether extracts are washed with saturated sodium chloride
  3. dry with materialdried over anhydrous potassium carbonate
  4. filtrationFiltration and concentration under reduced pressure
  5. customgives a pale orange solid which
  6. customis then chromatographed on silica gel
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-3fd638adb32a4360a991c6cfa504818d
Source dataset
uspto-grants-2002_04
Patent number
US06380243B1

Reaction notes

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