Ethyl trifluoroacetate → 1-(4-Chloro-2-fluorophenyl)-2,2,2-trifluoroethan-1-one

HRID 409914Notes

Reaction equation

HRID 409914 reaction equation
[Li]CCCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10](I)=[C:9]([F:14])[CH:8]=1.[F:15][C:16]([F:23])([F:22])[C:17](OCC)=[O:18]>C1COCC1>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:17](=[O:18])[C:16]([F:23])([F:22])[F:15])=[C:9]([F:14])[CH:8]=1

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 27365624-Chloro-2-fluoro-1-iodobenzeneHCID 178418339Butyllithium

Product 1

HCID 247268361-(4-Chloro-2-fluorophenyl)-2,2,2-trifluoroethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of n-BuLi (1.6 M in hexanes, 4.68 mmol, 2.93 mL) in dry THF was slowly added 4-chloro-2-fluoro-1-iodo-benzene 19a (3.9 mmol, 1.0 g) at −78° C. under N2. The mixture was stirred for 1 h at −78° C. and ethyl trifluoroacetate 18b (0.51 mL, 4.29 mmol) was added. The reaction was allowed to warm to room temperature overnight and was quenched with saturated aqueous NH4Cl solution. The mixture was extracted with EtOAc. The organic extracts were concentrated and purified by flash column chromatography (silica gel, 15% EtOAc/hexanes) to give compound 19b.

Workup

  1. customat −78° C.
  2. temperatureto warm to room temperature overnight
  3. customwas quenched with saturated aqueous NH4Cl solution
  4. extractionThe mixture was extracted with EtOAc
  5. concentrationThe organic extracts were concentrated
  6. custompurified by flash column chromatography (silica gel, 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b8441806b14e47339e4f655737e7b719
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

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