(2,6-Difluoro-3,5-dimethoxy-phenyl)-carbamic Acid Tert-Butyl Ester → 2,6-Difluoro-3,5-dimethoxybenzenamine

HRID 459945Notes

Reaction equation

HRID 459945 reaction equation
C(OC(=O)[NH:7][C:8]1[C:13]([F:14])=[C:12]([O:15][CH3:16])[CH:11]=[C:10]([O:17][CH3:18])[C:9]=1[F:19])(C)(C)C>FC(F)(F)C(O)=O>[F:14][C:13]1[C:12]([O:15][CH3:16])=[CH:11][C:10]([O:17][CH3:18])=[C:9]([F:19])[C:8]=1[NH2:7]

Participants

3

Reactant 1

HCID 86590945(2,6-Difluoro-3,5-dimethoxy-phenyl)-carbamic Acid Tert-Butyl Ester

Product 1

HCID 102618922,6-Difluoro-3,5-dimethoxybenzenamineYield 97%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To 34.6 g (0.12 mol) of (2,6-difluoro-3,5-dimethoxy-phenyl)-carbamic acid tert-butyl ester, 120 mL of trifluoroacetic acid was added to give a homogeneous solution which was stirred at room temperature for 30 minutes. After 30 min., 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 twice with diethylether. Combined diethylether layers were washed once with brine, dried over sodium sulfate, filtered and evaporated to give 22 g (97%) of title compound. MS (APCI) (m+1)/z 190.1.

Workup

  1. customto give a homogeneous solution which
  2. waitAfter 30 min.
  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 twice with diethylether
  6. washCombined diethylether layers were washed once with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-f425581ce63947c2a19ca9b8f355ec1f
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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