Pyridine → Methyl 4-methanesulfonyl-2-methyl-3-(trifluoromethanesulfonyl)oxybenzoate

HRID 1585464Notes

Reaction equation

[OH:1][C:2]1[C:3]([CH3:16])=[C:4]([CH:9]=[CH:10][C:11]=1[S:12]([CH3:15])(=[O:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6].N1C=CC=CC=1.[F:23][C:24]([F:30])([F:29])[S:25](O)(=[O:27])=[O:26]>C(Cl)Cl>[CH3:15][S:12]([C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([CH3:16])[C:2]=1[O:1][S:25]([C:24]([F:30])([F:29])[F:23])(=[O:27])=[O:26])(=[O:14])=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

8.8 g (0.036 mol) of methyl 3-hydroxy-4-methanesulfonyl-2-methyl-benzoate was dissolved in 100 ml of methylene chloride, and 8.3 g (0.11 mol) of pyridine was added. After the solution was cooled to 0° C., 12.2 g (0.043 mol) of anhydrous trifluoromethanesulfonic acid was added. After stirring at room temperature for 1 hour, the reaction mixture was washed with 1N hydrochloric acid and subsequently with saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 13.5 g of methyl 4-methanesulfonyl-2-methyl-3-(trifluoromethanesulfonyl)oxybenzoate. Yield=99%.

Workup

washthe reaction mixture was washed with 1N hydrochloric acid and subsequently with saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-7719549e4b174447b74d31accaeae9a0
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05939360

Reaction notes

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