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

HRID 2042069Notes

Reaction equation

HRID 2042069 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-d24cbc16525f47e091667f0e6be63144
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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