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

HRID 343965Notes

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 of 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 solution
dry with materialdried 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-4b0aa0075a5346299777906c0fbbca41
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05863930

Reaction notes

Loading…