1-Fluoro-4-methanesulfonyl-2-nitrobenzene → 2-Fluoro-5-(methylsulfonyl)aniline

HRID 2390153

Reaction equation

HRID 2390153 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([N+:12]([O-])=O)[CH:6]=1)(=[O:4])=[O:3].[H][H]>CO.[Pd]>[F:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][C:7]=1[NH2:12]

Participants

5

Reactant 2

HCID 3131371-Fluoro-4-methanesulfonyl-2-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 27746372-Fluoro-5-(methylsulfonyl)anilineYield 80.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-fluoro-3-nitrophenyl methyl sulfone (ABCR; 1.50 g; 6.84 mmol) and 10% Pd/C (100 mg) in MeOH (30 ml) was placed in a PARR reactor and treated with a pressure of 15 atm of hydrogen for 2 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated to dryness affording the title compound (1.04 g, 80%).

Workup

  1. customwas placed in a PARR reactor
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-e49b72b3ec1c4edd9bb1fee12d992c05
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Linked notes

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