Sodium Bicarbonate → Ethyl alpha-fluoro-4-chlorophenylacetate

HRID 1192370

反応式

HRID 1192370 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 13194587Ethyl alpha-fluoro-4-chlorophenylacetate収率 69.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

(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).

後処理

  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)

出典と根拠

ORDレコード
ord-4b05ccb3bbd649179c383edfa00bbab8
出典データセット
uspto-grants-2014_03
特許番号
US08680114B2

関連ノート

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