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

HRID 250835노트

반응식

HRID 250835 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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%

후처리

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

출처 및 근거

ORD 기록
ord-e025e15aeaf14fde97eea05cd14db590
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863332B2

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