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

HRID 6899

反応式

HRID 6899 の反応式
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]

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 72583,4-DichlorophenolHCID 10796Cesium carbonateHCID 131585835-Fluoro-2-iodobenzoic acid2 回

生成物 1

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

試薬・触媒・溶媒 4

HCID 2734996copper(II) trifluoromethanesulfonate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fa247d297f624cf2b98f0abe5ea5ce3a
出典データセット
uspto-grants-2006_08
特許番号
US07084165B2

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