Water → Methyl 5-acetyl-2-(2-fluorophenylamino)-3,4-difluorobenzoate

HRID 558245Notes

Reaction equation

HRID 558245 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:18]([F:19])=[C:17]([F:20])[C:16]([C:21]#[C:22][Si](C)(C)C)=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12].[OH:27]S(O)(=O)=O.O>CC(C)=O>[C:21]([C:16]1[C:17]([F:20])=[C:18]([F:19])[C:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:27])[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 59519400Methyl 2-(2-fluorophenylamino)-3,4-difluoro-5-((trimethylsilyl)ethynyl)benzoate

Product 1

HCID 59519431Methyl 5-acetyl-2-(2-fluorophenylamino)-3,4-difluorobenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 2-(2-fluorophenylamino)-3,4-difluoro-5-((trimethylsilyl)ethynyl)benzoate (9 mmol, 3.5 g), HgSO4 (9 mmol, 2.67 g), and cone. H2SO4 (18 mmol, 0.96 ml) in acetone:H2O (70:12 ml) was refluxed at 65° C. overnight. The mixture was concentrated, diluted with EtOAc, and washed with water and brine. The organic fractions are combined, dried over MgSO4 and concentrated under reduced pressure. The crude material (brown solid) was triturated with MeOH and the precipitate was filtered, washed with additional MeOH and dried to yield the desired product in 60% (1.78 g).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material (brown solid) was triturated with MeOH
  7. filtrationthe precipitate was filtered
  8. washwashed with additional MeOH
  9. customdried

Sources & evidence

ORD record
ord-86a4ca13797f4ac9902184a06f95ec4c
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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