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

HRID 2279023Notes

Reaction equation

HRID 2279023 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

A solution of 1-benzyloxy-3-fluoro-2-methyl-4-nitro-benzene (8 g, 0.031 mol) in MeOH (100 mL) was treated with Pd/C (10%) and hydrogenated (30 psi) for 2 h. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo to afford 4-amino-3-fluoro-2-methyl-phenol (4.2 g, 96% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.61 (s, 1 H), 6.36 (m, 2 H), 4.28 (s, 2 H), 1.96 (s, 3H); MS (ESI) m/z: 142.1 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-38315b36d6aa42ec9e8c561e2fdbe943
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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