1-(Benzyloxy)-3-fluoro-2-methyl-4-nitrobenzene → 4-Amino-3-fluoro-2-methylphenol

HRID 1711649Notes

Reaction equation

HRID 1711649 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[CH3:19])C1C=CC=CC=1>CO.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([CH3:19])[C:11]=1[F:18]

Participants

4

Reactant 1

HCID 667290181-(Benzyloxy)-3-fluoro-2-methyl-4-nitrobenzene

Product 1

HCID 552890104-Amino-3-fluoro-2-methylphenolYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Benzyloxy-3-fluoro-2-methyl-4-nitrobenzene (8 g, 0.031 mol) and 10% Pd—C (1 g) were combined in methanol (100 mL) and the mixture was stirred under an H2 atmosphere (1 atm) overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give 4-amino-3-fluoro-2-methylphenol (4.2 g, 96% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.61 (s, 1H), 6.42 (t, J=8.4 Hz, 1H), 7.11 (d, J=8.4 Hz, 1H), 4.28 (s, 2H), 1.96 (s, 3H); MS (ESI) m/z: 142.1 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-55e22a574b20497c9853c1d6b919405e
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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