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

HRID 250835ノート

反応式

HRID 250835 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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%

後処理

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

出典と根拠

ORDレコード
ord-e025e15aeaf14fde97eea05cd14db590
出典データセット
uspto-grants-2011_01
特許番号
US07863332B2

反応ノート

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