Hydrochloric Acid → (RS)-(2,6-difluoro-4-trifluoromethanesulfonyloxy-phenyl)-ethoxy-acetic acid ethyl ester

HRID 1247373Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][C:12]([OH:16])=[CH:11][C:10]=1[F:17])[O:6][CH2:7][CH3:8])[CH3:2].[O:19](S(C(F)(F)F)(=O)=O)[S:20]([C:23]([F:26])([F:25])[F:24])(=O)=[O:21].Cl>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][C:12]([O:16][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:21])=[O:19])=[CH:11][C:10]=1[F:17])[O:6][CH2:7][CH3:8])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (RS)-(2,6-difluoro-4-hydroxy-phenyl)-ethoxy-acetic acid ethyl ester (500 mg) in pyridine (5 ml) was placed under N2 and cooled to 0° C. Tf2O (813 mg) was added and the resulting solution was left to stir in the ice bath. After 18 h the reaction mixture was poured on a mixture of 50 ml 1 N HCl and ice. The product was extracted with AcOEt. The organic layer was washed with more 1 N HCl (50 ml), water (50 ml) and brine (30 ml). The aqueous layers were extracted with more AcOEt. After drying (MgSO4) the solvent was evaporated to obtain 738 mg (98%) of (RS)-(2,6-difluoro-4-trifluoromethanesulfonyloxy-phenyl)-ethoxy-acetic acid ethyl ester. Yellow oil. MS 393.4 ([M+H]+).

Workup

waitthe resulting solution was left
extractionThe product was extracted with AcOEt
washThe organic layer was washed with more 1 N HCl (50 ml), water (50 ml) and brine (30 ml)
extractionThe aqueous layers were extracted with more AcOEt
dry with materialAfter drying (MgSO4) the solvent
customwas evaporated

Sources & evidence

ORD record: ord-4d14dee68f2349f289c201fd70f28d2e
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129238B2

Reaction notes

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