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

HRID 1670217Notes

Reaction equation

HRID 1670217 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[OH:11]>CO.[Pt]=O>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[OH:11]

Participants

4

Reactant 1

HCID 98252-Fluoro-4-nitrophenol

Product 1

HCID 2735918Phenol, 4-amino-2-fluoro-Yield 101.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of platinum oxide (0.010 g) and 2-fluoro-4-nitrophenol (Aldrich, 1.24 g, 7.78 mmol, 1.0 eq) in MeOH (100 ml) were stirred under a H2 atmosphere at 50 psi at room temperature. The reaction mixture was filtered through celite and the filtrate concentrated in vacuo to afford the title compound (1.00 g, 100%), as a solid which was used without further purification. 1H NMR (DMSO-d6) δ 8.57 (s, 1H), 6.46-6.47 (m, 1H), 6.33-6.46 (m, 1H), 6.19-6.21 (m, 1H), 4.79 (s, 2H); MS (ESI+) m/z 128 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-fa9900939725467fa05174309685f479
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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