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Potassium Carbonate → 5-Methanesulfonyl-2-(2,2,3,3,3-pentafluoro-propoxy)-benzoic acid methyl ester

HRID 2251180
Notes
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Reaction equation

HRID 2251180 reaction equation
[CH3:1][S:2]([C:5]1[CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:8]([OH:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:16][C:17]([F:31])([C:27]([F:30])([F:29])[F:28])[CH2:18]OS(C(F)(F)F)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:13][O:12][C:10](=[O:11])[C:9]1[CH:14]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=[CH:7][C:8]=1[O:15][CH2:18][C:17]([F:31])([F:16])[C:27]([F:30])([F:29])[F:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27760192,2,3,3,3-Pentafluoropropyl trifluoromethanesulfonateHCID 235031632-Hydroxy-5-methylsulfonylbenzoic acid methyl ester

Product 1

HCID 866007065-Methanesulfonyl-2-(2,2,3,3,3-pentafluoro-propoxy)-benzoic acid methyl esterYield 55.9%

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent

Procedure

A solution of methyl 5-(methanesulfonyl)salicylate [101371-44-2] (0.50 g), trifluoro-methanesulfonic acid 2,2,3,3,3-pentafluoro-propyl ester (0.67 g) and potassium carbonate (0.60 g) in acetone was stirred at 60° C. for 5 hours. The reaction mixture was then concentrated in vacuo and purified by column chromatography (SiO2) to yield the title compound as a white solid (0.44 g). MS (m/e): 363.1 (M+H+, 100%).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. custompurified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-15558b9011854f77a1d57ca88b9324fc
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07319099B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes