Trifluoroacetic acid → 2-Fluoro-3,5-dimethoxyaniline

HRID 459948Notes

Reaction equation

HRID 459948 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([O:16][CH3:17])[C:9]=1[F:18])(C)(C)C.FC(F)(F)C(O)=O>>[F:18][C:9]1[C:10]([O:16][CH3:17])=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:8]=1[NH2:7]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69030856tert-Butyl (2-fluoro-3,5-dimethoxyphenyl)carbamate

Product 1

HCID 153245152-Fluoro-3,5-dimethoxyanilineYield 95.5%

Procedure

To 56.6 g (0.21 mol) of (2-fluoro-3,5-dimethoxy-phenyl)-carbamic acid tert-butyl ester, 184 mL of trifluoroacetic acid was added to give a homogeneous solution which was stirred at room temperature for 30 minutes. After 30 minutes, the reaction mixture was concentrated in vacuo. To the residue, a saturated solution of sodium bicarbonate was carefully added to pH 8. The resulting suspension was extracted two times with diethylether. The combined diethylether layers were washed one time with brine, dried over sodium sulfate, filtered and evaporated to give 34.1 g (95.5%) of title compound. MS (APCI) (m+1)/z 172.0.

Workup

  1. customto give a homogeneous solution which
  2. waitAfter 30 minutes
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additionTo the residue, a saturated solution of sodium bicarbonate was carefully added to pH 8
  5. extractionThe resulting suspension was extracted two times with diethylether
  6. washThe combined diethylether layers were washed one time with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-d016498d2be840c49c8f8d867d4f0593
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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