Pyridine → Methyl 2,4-dichloro-6-{[(trifluoromethyl)sulfonyl]oxy}benzoate

HRID 1374164Notes

Reaction equation

HRID 1374164 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([OH:12])[C:3]=1[C:4]([O-:6])=[O:5].N1C=CC=C[CH:14]=1.[F:19][C:20]([F:26])([F:25])[S:21](O)(=[O:23])=[O:22]>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([O:12][S:21]([C:20]([F:26])([F:25])[F:19])(=[O:23])=[O:22])[C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62406Trifluoromethanesulfonic acidHCID 178524831HCID 178524831, compound

Product 1

HCID 21075880Methyl 2,4-dichloro-6-{[(trifluoromethyl)sulfonyl]oxy}benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,4-dichloro-6-hydroxybenzoate (4.64 g, 20.99 mmol) and pyridine (1.87 mL, 23.09 mmol) in 100 mL CH2Cl2 was cooled to 0° C. Trifluoromethanesulfonic acid (4.94 mL, 29.39 mmol) was added, and the solution was stirred for 2 h. The reaction mixture was washed with aqueous sodium bicarbonate, aqueous copper sulfate and brine, dried over Na2SO4, filtered and concentrated to provide methyl 2,4-dichloro-6-{[(trifluoromethyl)sulfonyl]oxy}-benzoate that gave proton NMR spectra consistent with theory.

Workup

  1. washThe reaction mixture was washed with aqueous sodium bicarbonate, aqueous copper sulfate and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-be40886607734cce96686ce804560c2c
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

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