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

HRID 1711487Notes

Reaction equation

HRID 1711487 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([OH:13])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].N1C=CC=CC=1.[F:20][C:21]([F:27])([F:26])[S:22](O)(=[O:24])=[O:23]>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([O:13][S:22]([C:21]([F:27])([F:26])[F:20])(=[O:24])=[O:23])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62406Trifluoromethanesulfonic acidHCID 21075879Methyl 2,4-dichloro-6-hydroxybenzoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the above ester (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-17f56ab9fe184796b4070e4abcfb404c
Source dataset
uspto-grants-2010_09
Patent number
US07790754B2

Reaction notes

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