Ethyl trifluoroacetate → 2,2,2-Trifluoro-1-(3,4,5-trichlorophenyl)ethan-1-one

HRID 68575Notes

Reaction equation

HRID 68575 reaction equation
[Li]CCCC.Br[C:7]1[CH:8]=[CH:9][C:10]([Cl:15])=[C:11]([Cl:14])[C:12]=1[Cl:13].[F:16][C:17]([F:24])([F:23])[C:18](OCC)=[O:19]>C(OCC)C>[F:16][C:17]([F:24])([F:23])[C:18]([C:8]1[CH:9]=[C:10]([Cl:15])[C:11]([Cl:14])=[C:12]([Cl:13])[CH:7]=1)=[O:19]

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 1847861-Bromo-2,3,4-trichlorobenzeneHCID 178418339Butyllithium

Product 1

HCID 580775942,2,2-Trifluoro-1-(3,4,5-trichlorophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-BuLi (16.5 ml, 2.5M in hexane) is added over 20 minutes to a solution of 5-bromo-1,2,6-trichloro-benzene (10.2 g) in diethyl ether (150 ml) under nitrogen at −78° C. After 20 minutes at −78° C., a solution of ethyl trifluoroacetate (5.15 ml) in diethyl ether (50 ml) is added over 15 minutes to the reaction mixture. After 40 minutes at −78° C., the reaction mixture is slowly warmed up to room temperature and then quenched with a saturated aqueous solution of NH4Cl. The aqueous phase is extracted three times with diethyl ether. The combined organic phases are dried over Na2SO4 and concentrated in vacuo. The crude product is purified by vacuum distillation to yield 2,2,2-trifluoro-1-(3,4,5-trichloro-phenyl)-ethanone (9.20 g) as a yellow solid.

Workup

  1. waitAfter 40 minutes at −78° C.
  2. customquenched with a saturated aqueous solution of NH4Cl
  3. extractionThe aqueous phase is extracted three times with diethyl ether
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. distillationThe crude product is purified by vacuum distillation

Sources & evidence

ORD record
ord-4f30023f0bea449381694a6dea386bf1
Source dataset
uspto-grants-2014_09
Patent number
US08822466B2

Reaction notes

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