2-Fluoro-1-(2-(methylsulfonyl)ethyl)-4-nitrobenzene → 3-Fluoro-4-(2-(methylsulfonyl)ethyl)aniline

HRID 1843030Notes

Reaction equation

HRID 1843030 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14]>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[NH2:8]

Participants

4

Reactant 1

HCID 708167962-Fluoro-1-(2-(methylsulfonyl)ethyl)-4-nitrobenzene

Product 1

HCID 866721743-Fluoro-4-(2-(methylsulfonyl)ethyl)anilineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Fluoro-1-(2-(methylsulfonyl)ethyl)-4-nitrobenzene (700 mg, 2.83 mmol) was dissolved in ethyl acetate (7 mL), and to the solution was added (10%) Pd/C (70 mg) under argon atmosphere which was subjected to hydrogenation in a Parr apparatus and the reaction was continued to stir for 2 h. The reaction mixture was filtered through celite and was washed thoroughly with ethyl acetate and was concentrated under reduced pressure to obtain 3-fluoro-4-(2-(methylsulfonyl)ethyl)aniline (590 mg, 96%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwas washed thoroughly with ethyl acetate
  3. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-a5f1004438e04791b8cee14ed37a6cca
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

Loading…