2-Fluoro-4-nitrophenol → Phenol, 4-amino-2-fluoro-

HRID 1670215Notes

Reaction equation

HRID 1670215 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[OH:11].[Cl-].[NH4+]>O1CCCC1.CO.[Zn]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([OH:11])=[C:2]([F:1])[CH:7]=1

Participants

6

Reactant 2

HCID 98252-Fluoro-4-nitrophenolHCID 25517Ammonium Chloride

Product 1

HCID 2735918Phenol, 4-amino-2-fluoro-

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-fluoro-4-nitrophenol (Avacado, 1.00 g, 6.37 mmol) in 4 mL of tetrahydrofuran and 6 mL of methanol at 0° C. was added zinc dust (2.08 g, 31.8 mmol, <10 micron) followed by ammonium chloride (1.70 g, 31.8 mmol). The mixture was stirred at room temperature overnight. The heterogeneous mixture was filtered through a thin pad of Celite® with methanol and the filtrate was concentrated in vacuo to give 4-amino-2-fluorophenol as a brown solid which was used without further purification (656 mg, 81%).

Workup

  1. filtrationThe heterogeneous mixture was filtered through a thin pad of Celite® with methanol
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-36aadacccc7249ea9e3e0d6825255e78
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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