Hydrochloric Acid → 5-Ethanesulfonyl-2-fluoro-benzoic acid

HRID 1352257Notes

Reaction equation

HRID 1352257 reaction equation
C([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])[CH:8]=[CH:7][C:6]=1[F:16])C.O.O.[OH-].[Li+].Cl>O1CCCC1>[CH2:14]([S:11]([C:9]1[CH:8]=[CH:7][C:6]([F:16])=[C:5]([CH:10]=1)[C:4]([OH:17])=[O:3])(=[O:12])=[O:13])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 58863356HCID 58863356, compound

Product 1

HCID 211002995-Ethanesulfonyl-2-fluoro-benzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 10.8 mmol 5-ethanesulfonyl-2-fluoro-benzoic acid ethyl ester in 26 ml tetrahydrofuran was added 26 ml water and 16.1 mmol lithium hydroxide monohydrate and the reaction mixture was stirred at room temperature for 45 minutes. After such time, the reaction mixture was acidified with 1N HCl, tetrahydrofuran was evaporated and the aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo to give the title compound as a white solid (96%). MS (m/e): 232.1 ([M+, 100%).

Workup

  1. customwas evaporated
  2. extractionthe aqueous phase was extracted twice with dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e55a39a26772462cb2883bf7fa889f19
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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