Ammonium formate → 5-Amino-2-tert-butyl-4-trifluoromethyl-phenol

HRID 401334Notes

Reaction equation

HRID 401334 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[C:8]([N+:15]([O-])=O)=[CH:7][C:6]=1[O:18]CC1C=CC=CC=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CCO.[Pd]>[NH2:15][C:8]1[C:9]([C:11]([F:12])([F:13])[F:14])=[CH:10][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[C:6]([OH:18])[CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 574702381-Tert-butyl-2-(benzyloxy)-5-(trifluoromethyl)-4-nitrobenzene

Product 1

HCID 574702395-Amino-2-tert-butyl-4-trifluoromethyl-phenolYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a refluxing solution of 1-tert-butyl-2-(benzyloxy)-5-(trifluoromethyl)-4-nitrobenzene (353 mg, 1.0 mmol) and ammonium formate (350 mg, 5.4 mmol) in EtOH (10 mL) was added 10% Pd—C (245 mg). The mixture was refluxed for additional 2 h, cooled to room temperature and filtered through Celite. After removal of solvent, the residue was purified by column chromatography to give 5-Amino-2-tert-butyl-4-trifluoromethyl-phenol (C-14) (120 mg, 52%). 1H NMR (400 MHz, CDCl3) δ 7.21 (s, 1H), 6.05 (s, 1H), 1.28 (s, 9H); HPLC ret. time 3.46 min, 10-99% CH3CN, 5 min run; ESI-MS 234.1 m/z (MH+).

Workup

  1. temperatureThe mixture was refluxed for additional 2 h
  2. filtrationfiltered through Celite
  3. customAfter removal of solvent
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6fe781a5a81b45b0bf773d541858ed5b
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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