Sodium Bicarbonate → Ethyl alpha-fluoro-4-chlorophenylacetate

HRID 1192370Notes

Reaction equation

HRID 1192370 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)O)[CH3:2].COCCN(S(F)(F)[F:25])CCOC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:14])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[F:25])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 12373588Ethyl (4-chlorophenyl)(hydroxy)acetate

Product 1

HCID 13194587Ethyl alpha-fluoro-4-chlorophenylacetateYield 69.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

(4-Chlorophenyl)-hydroxy-acetic acid ethyl ester (10.0 g, 46.6 mmol) in DCM (35 mL) was cannulated into a solution of [bis(2-methoxyethyl)amino]sulfur trifluoride (9.45 mL, 51.3 mmol) in DCM (35 mL) cooled at −78° C. After being stirred for 12 hours and allowed to warm to ambient temperature, the mixture was poured into saturated aqueous NaHCO3. The mixture was extracted with DCM and the organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude material was chromatographed (SiO2) using DCM as eluent to give (4-chlorophenyl)-fluoroacetic acid ethyl ester as a colorless oil (7.0 g).

Workup

  1. temperatureto warm to ambient temperature
  2. extractionThe mixture was extracted with DCM
  3. dry with materialthe organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was chromatographed (SiO2)

Sources & evidence

ORD record
ord-4b05ccb3bbd649179c383edfa00bbab8
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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