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

HRID 250835Notes

Reaction equation

HRID 250835 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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%

Workup

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

Sources & evidence

ORD record
ord-e025e15aeaf14fde97eea05cd14db590
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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