Ammonium formate → 2-Tert-butyl-5-amino-4-fluorophenol

HRID 2370252Notes

Reaction equation

HRID 2370252 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-])=O)=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CCO.[Pd]>[C:1]([C:5]1[CH:10]=[C:9]([F:11])[C:8]([NH2:12])=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57470218HCID 57470218, compound

Product 1

HCID 574702192-Tert-butyl-5-amino-4-fluorophenolYield 159.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a refluxing solution of 2-tert-butyl-4-fluoro-5-nitrophenol (400 mg, 1.88 mmol) and ammonium formate (400 mg, 6.1 mmol) in EtOH (20 mL) was added 5% Pd—C (260 mg). The mixture was refluxed for additional 1 h, cooled and filtered through Celite. The solvent was removed by evaporation to give 2-tert-butyl-5-amino-4-fluorophenol (C-7) (550 mg, 83%). 1H NMR (400 MHz, DMSO-d6) δ 8.83 (br s, 1H), 6.66 (d, J=13.7 Hz, 1H), 6.22 (d, J=8.5 Hz, 1H), 4.74 (br s, 2H), 1.26 (s, 9H); HPLC ret. time 2.58 min, 10-99% CH3CN, 5 min run; ESI-MS 184.0 m/z (MH+).

Workup

  1. temperatureThe mixture was refluxed for additional 1 h
  2. temperaturecooled
  3. filtrationfiltered through Celite
  4. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-ef348a05c063495aafc2bb7abedd7c00
Source dataset
uspto-grants-2014_04
Patent number
US08710075B2

Reaction notes

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