1-(Benzyloxy)-2,3-difluoro-4-nitrobenzene → 4-Amino-2,3-difluorophenol

HRID 1098546Notes

Reaction equation

HRID 1098546 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([F:18])[C:10]=1[F:19])C1C=CC=CC=1>CO.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([F:19])[C:11]=1[F:18]

Participants

4

Reactant 1

HCID 574708771-(Benzyloxy)-2,3-difluoro-4-nitrobenzene

Product 1

HCID 27787664-Amino-2,3-difluorophenolYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-benzyloxy-2,3-difluoro-4-nitro-benzene (14 g, 52.8 mmol) in MeOH (200 mL) was stirred with Pd/C (10%, 1.4 of 1.3 mmol) under a hydrogen atmosphere (30 psi) for 2 h. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo to afford 4-amino-2,3-difluorophenol (7 g, 92.1% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.05 (s, 1 H), 6.45 (t, J=8.8 Hz, 1 H), 6.34 (t, J=9.2 Hz, 1 H), 4.67 (s, 2 H); MS (ESI) m/z: 146.1[M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0388daa6e8c9491c9c6f8f4bd04c545f
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

Loading…