Trifluoroacetic acid → Methyl 4-amino-2,6-difluorobenzoate

HRID 56623Notes

Reaction equation

HRID 56623 reaction equation
C(O)(C(F)(F)F)=O.C(OC([NH:15][C:16]1[CH:25]=[C:24]([F:26])[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([F:27])[CH:17]=1)=O)(C)(C)C>ClCCl>[NH2:15][C:16]1[CH:17]=[C:18]([F:27])[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:24]([F:26])[CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15112844Methyl 4-((tert-butoxycarbonyl)amino)-2,6-difluorobenzoate

Product 1

HCID 23001755Methyl 4-amino-2,6-difluorobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At RT, 0.5 ml of TFA was added to a solution of 36 mg (0.125 mmol) of methyl 4-[(tert-butoxycarbonyl)amino]-2,6-difluorobenzoate in 1 ml of dichloromethane, and the mixture was stirred at RT for 30 min. The reaction mixture was then concentrated under reduced pressure and the residue was co-evaporated repeatedly with dichloromethane and toluene and dried under reduced pressure. The crude product was used for the next step without purification. Yield: 24 mg (quant.)

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customdried under reduced pressure
  3. customThe crude product was used for the next step without purification

Sources & evidence

ORD record
ord-28107a5f968b43d280fd462d941a000e
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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