Hydrochloric Acid → Methyl 2-methoxy-4-trifluoromethane-sulfonyloxybenzoate

HRID 2220616Notes

Reaction equation

HRID 2220616 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([O:27][CH3:28])[CH:18]=1.N1C=CC=CC=1.Cl>C(Cl)Cl.C(OCC)(=O)C>[CH3:28][O:27][C:19]1[CH:18]=[C:17]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 12532676Methyl 4-hydroxy-2-methoxybenzoate

Product 1

HCID 23282575Methyl 2-methoxy-4-trifluoromethane-sulfonyloxybenzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoromethanesulfonic anhydride (2.24 mL) was added to an ice-cooled mixture of methyl 4-hydroxy-2-methoxybenzoate (2.02 g) and pyridine (0.135 mL) in methylene chloride (15 mL) with stirring. The mixture was stirred at room temperature for 30 minutes, and poured into a mixture of hydrochloric acid and ethyl acetate. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford methyl 2-methoxy-4-trifluoromethanesulfonyloxybenzoate (3.49 g).

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c30eecc05f194bd5b4d5a4467c982e0b
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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