Hydrochloric Acid → 2-(3,4-Dichlorophenoxy)-5-fluoro-benzoic acid

HRID 6899

반응식

HRID 6899 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:9]=[C:10]([OH:15])[CH:11]=[CH:12][C:13]=1[Cl:14].[F:16][C:17]1[CH:18]=[CH:19][C:20](I)=[C:21]([CH:25]=1)[C:22]([OH:24])=[O:23].Cl>C1(C)C=CC=CC=1.O.CCOC(C)=O.FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[Cl:14])[O:15][C:20]1[CH:19]=[CH:18][C:17]([F:16])=[CH:25][C:21]=1[C:22]([OH:24])=[O:23]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 72583,4-DichlorophenolHCID 10796Cesium carbonateHCID 131585835-Fluoro-2-iodobenzoic acid2회

생성물 1

HCID 220192772-(3,4-Dichlorophenoxy)-5-fluoro-benzoic acid

시약·촉매·용매 4

HCID 2734996copper(II) trifluoromethanesulfonate촉매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

Under N2 in a round-bottomed flask fitted with a reflux condenser and magnetic stirrer were placed 6.37 g (19.55 mmol) of cesium carbonate and 3.2 g (19.55 mmol) of 3,4-dichlorophenol (both from Aldrich Chem. Co., Milwaukee, Wis.) in 60 mL of anhydrous toluene. After stirring the mixture for 5 min., 89 mg (0.24 mmol) of copper (II) trifluoromethanesulfonate (copper triflate) and 0.26g (9.78 mmol) of 5-fluoro-2-iodobenzoic acid (prepared according to the method in Collection of Czechoslovakian Chemical Communications, 1975, vol. 40, p728) were added and the mixture was heated to reflux overnight. Progress of the reaction was monitored using thin layer chromatography (tic), eluting with CHCl3:CH3OH:AcOH (9:1:0.5). After allowing the reaction to cool to room temperature, the mixture was diluted with water and EtOAc; the aqueous layer was acidified with 6 N HCl and re-extracted with additional EtOAc. The organic layers were combined, washed with H2O and saturated NaCl and dried over MgSO4. Removal of the solvent in vacuo gave a dark brown colored oil, 2.6 g, as a mixture of title product and unreacted 5-fluoro-2-iodobenzoic acid.

후처리

  1. customUnder N2 in a round-bottomed flask fitted with a reflux condenser and magnetic stirrer
  2. customaccording to the method in Collection of Czechoslovakian Chemical Communications, 1975, vol. 40, p728)
  3. additionwere added
  4. temperaturethe mixture was heated
  5. temperatureto reflux overnight
  6. washeluting with CHCl3:CH3OH:AcOH (9:1:0.5)
  7. customthe reaction
  8. extractionre-extracted with additional EtOAc
  9. washwashed with H2O and saturated NaCl
  10. dry with materialdried over MgSO4
  11. customRemoval of the solvent in vacuo
  12. customgave a dark brown colored oil, 2.6 g

출처 및 근거

ORD 기록
ord-fa247d297f624cf2b98f0abe5ea5ce3a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084165B2

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