1,4-Dibromobenzene → 1-(4-Bromophenyl)-2,2-difluoroethan-1-one

HRID 216329Notes

Reaction equation

HRID 216329 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1.[F:14][C:15](F)([F:21])[C:16](OCC)=[O:17]>C(OCC)C>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C:16](=[O:17])[CH:15]([F:21])[F:14])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 78041,4-DibromobenzeneHCID 9794Ethyl trifluoroacetateHCID 178418339Butyllithium

Product 1

HCID 152713931-(4-Bromophenyl)-2,2-difluoroethan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (1.6 M in hexane) (165 mL, 0.264 mmol) was added dropwise to a −78° C. solution of 1,4-dibromobenzene (60.1 g) in diethyl ether (500 mL). After stirring at −78° C. for 2 h, ethyl trifluoroacetate (40 g) was added dropwise and the mixture was allowed to warm to ambient temperature overnight. The reaction mixture was cooled to −20° C., quenched with saturated aqueous ammonium chloride and extracted with ether. The combined organic phases were washed with saturated aqueous sodium bicarbonate, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with petroleum ether/ethyl acetate (20:1) afforded the title compound.

Workup

  1. temperatureto warm to ambient temperature overnight
  2. temperatureThe reaction mixture was cooled to −20° C.
  3. customquenched with saturated aqueous ammonium chloride
  4. extractionextracted with ether
  5. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44d176d5bc9644c0baea507bd8567ed2
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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