Sodium Bicarbonate → Ethyl alpha-fluoro-4-chlorophenylacetate

HRID 1192370

반응식

HRID 1192370 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

(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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4b05ccb3bbd649179c383edfa00bbab8
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680114B2

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