1-Fluoro-5-(3-fluorophenyl)-2-methyl-3-nitro-benzene → 3-Fluoro-5-(3-fluorophenyl)-2-methyl-aniline

HRID 1771727Notes

Reaction equation

HRID 1771727 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[CH:5]=[C:4]([N+:15]([O-])=O)[C:3]=1[CH3:18]>CCO.[Pd]>[F:1][C:2]1[C:3]([CH3:18])=[C:4]([CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[CH:7]=1)[NH2:15]

Participants

4

Reactant 1

HCID 894454551-Fluoro-5-(3-fluorophenyl)-2-methyl-3-nitro-benzene

Product 1

HCID 894453313-Fluoro-5-(3-fluorophenyl)-2-methyl-anilineYield 44%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-fluoro-5-(3-fluorophenyl)-2-methyl-3-nitro-benzene (4.0 g, 16.0 mmol, 1.0 eq) in EtOH (80 mL) was added to Pd/C (10%, 0.8 g) and the mixture stirred under hydrogen for 48 h. The catalyst was removed by filtration through celite and the compound purified by silica gel chromatography (petroleum ether:EtOAc, 20:1 to 10:1) to give the title compound as a white solid (1.54 g, 44%).

Workup

  1. customThe catalyst was removed by filtration through celite
  2. customthe compound purified by silica gel chromatography (petroleum ether:EtOAc, 20:1 to 10:1)

Sources & evidence

ORD record
ord-9171a96f95074d139f59f33396152dac
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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