Hydrochloric Acid → methyl(E)-3-(3-fluoro-4-trifluoromethanesulfonyloxyphenyl)acrylate

HRID 250835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 250835
S([O:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])(C(F)(F)F)(=O)=O.[F:16][C:17]1[CH:18]=[C:19](/[CH:24]=[CH:25]/[C:26]([O:28][CH3:29])=[O:27])[CH:20]=[CH:21][C:22]=1O.C(N(C(C)C)CC)(C)C.Cl>ClCCl.O>[F:16][C:17]1[CH:18]=[C:19](/[CH:24]=[CH:25]/[C:26]([O:28][CH3:29])=[O:27])[CH:20]=[CH:21][C:22]=1[O:8][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:10])=[O:11]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 67273036methyl(E)-3-(3-fluoro-4-hydroxyphenyl)acrylate

Produkt 1

HCID 86614973methyl(E)-3-(3-fluoro-4-trifluoromethanesulfonyloxyphenyl)acrylateAusbeute 102 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.40 mL (8.3 mmol, 1.1 eq) of triflic anhydride are added to a solution of 1.47 g (7.5 mmol, 1 eq) of methyl (E)-3-(3-fluoro-4-hydroxyphenyl)acrylate and 1.57 mL (9.0 mmol, 1.2 eq) of diisopropylethylamine in 10 mL of dichloromethane. The reaction mixture is stirred at room temperature overnight. The reaction medium is hydrolyzed in water, acidified with 1N hydrochloric acid solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over sodium sulfate. The solvent is evaporated off and 2.51 g of methyl (E)-3-(3-fluoro-4-trifluoromethanesulfonyloxyphenyl)acrylate are obtained in the form of a brown oil. Yield=100%

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is evaporated off

Quellen und Nachweise

ORD-Eintrag
ord-e025e15aeaf14fde97eea05cd14db590
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863332B2

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