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

HRID 30741Notes

Reaction equation

HRID 30741 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 (0.14 mL) in methylene chloride (15 mL) with stirring. The mixture was stirred at room temperature for 30 min, 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 min
  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-887166da898c4f14ba6a5603f09da6c5
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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