Trifluoromethanesulfonic anhydride → Methyl 3-chloro-4-[[(trifluoromethyl)sulfonyl]oxy]benzoate

HRID 234767Notes

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].[Cl:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=1O)[C:20]([O:22][CH3:23])=[O:21]>N1C=CC=CC=1>[Cl:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=1[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[C:20]([O:22][CH3:23])=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

5.5 ml of trifluoromethanesulphonic anhydride (33 mmol) are slowly added dropwise to a solution of 5.49 g methyl 3-chloro-4-hydroxy-benzoate (29.4 mmol) in 15 ml of pyridine at 0° C. After the reaction mixture has been stirred at 0° C. for 5 minutes and at room temperature for 4 hours, it is partitioned between water and ether. The organic phase is washed in succession with water, dilute hydrochloric acid, water and saturated sodium chloride. solution, dried over sodium sulphate and concentrated and the residue is chromatographed over silica gel using methylene chloride to give 8.93 g of a pale yellow thinly mobile oil [95.2% of theory, Rf 0.63 (hexane:ethyl acetate=3:1)].

Workup

customit is partitioned between water and ether
washThe organic phase is washed in succession with water, dilute hydrochloric acid, water and saturated sodium chloride
dry with materialsolution, dried over sodium sulphate
concentrationconcentrated
customthe residue is chromatographed over silica gel
customto give 8.93 g of a pale yellow thinly mobile oil [95.2% of theory, Rf 0.63 (hexane:ethyl acetate=3:1)]

Sources & evidence

ORD record: ord-0c0ba624942a4db78eefa85ee712f8f1
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05596006

Reaction notes

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