Trimethylsilyldiazomethane → Methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoate

HRID 558195Notes

Reaction equation

HRID 558195 reaction equation
[Br:1][C:2]1[C:3]([F:20])=[C:4]([F:19])[C:5]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:21][Si](C=[N+]=[N-])(C)C>C1COCC1.CO>[Br:1][C:2]1[C:3]([F:20])=[C:4]([F:19])[C:5]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:21])=[O:8]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 595193885-Bromo-3,4-difluoro-2-((2-fluorophenyl)amino)benzoic acid

Product 1

HCID 59519391Methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoateYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-3,4-difluoro-2-(2-fluorophenylamino)benzoic acid (3.0 g, 8.67 mmol) in a mixture of THF (15 ml) and MeOH (5 ml) was added (trimethylsilyl)diazomethane (5.63 ml, 2 M in Hexanes, 11.3 ml). After stirring for 4 h, the reaction was quenched with AcOH and diluted with EtOAc (100 ml). The organic solution was washed with H2O (50 ml) and brine (50 ml), dried over Na2SO4 and concentrated to dryness to give 2.83 g (91%) of methyl 5-bromo-3,4-difluoro-2-(2-fluorophenylamino)benzoate as a light yellow solid.

Workup

  1. customthe reaction was quenched with AcOH
  2. additiondiluted with EtOAc (100 ml)
  3. washThe organic solution was washed with H2O (50 ml) and brine (50 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a771bacddd864080a4671641cb33ef8c
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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