Sulfuric Acid → 5-Acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

HRID 917013Notes

Reaction equation

HRID 917013 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([C:10]#[C:11][Si](C)(C)C)[C:7]([F:16])=[C:6]([F:17])[C:5]=1[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25].[OH:27]S(O)(=O)=O>CC(C)=O>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([C:10](=[O:27])[CH3:11])[C:7]([F:16])=[C:6]([F:17])[C:5]=1[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 865967722-(2-Chlorophenylamino)-3,4-difluoro-5-trimethylsilanylethynylbenzoic acid methyl ester

Product 1

HCID 865967735-Acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl esterYield 73.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(2-chlorophenylamino)-3,4-difluoro-5-trimethylsilanylethynylbenzoic acid methyl ester (5) (79.4 mg, 0.20 mmol), HgSO4 (59.8 mg, 2.0 mmol), and conc. H2SO4 (0.02 mL, 0.40 mmol) in 80% aqueous acetone (2.5 mL), were refluxed for 48 hours. The reaction was concentrated under reduced pressure, and diluted with EtOAc. The organic layer was washed with water and brine, dried over MgSO4 and concentrated to give 50.1 mg (73%) of the desired product (6).

Workup

  1. temperaturewere refluxed for 48 hours
  2. concentrationThe reaction was concentrated under reduced pressure
  3. additiondiluted with EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f1091909b96c4ced82e988f58d17cb63
Source dataset
uspto-grants-2007_09
Patent number
US07271178B2

Reaction notes

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