1-Methanesulfonyl-3-nitro-5-trifluoromethylbenzene → 3-Methanesulfonyl-5-(trifluoromethyl)aniline

HRID 2200124Notes

Reaction equation

HRID 2200124 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([N+:15]([O-])=O)[CH:6]=1)(=[O:4])=[O:3]>CO.[Pd]>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1)[NH2:15])(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 684231001-Methanesulfonyl-3-nitro-5-trifluoromethylbenzene

Product 1

HCID 592861463-Methanesulfonyl-5-(trifluoromethyl)anilineYield 73.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Stir the mixture of 1-(methylsulfonyl)-3-nitro-5-(trifluoromethyl)benzene (2 g, 7.43 mmol), Pd/C (10%, 500 mg) in methanol (100 mL) under hydrogen atmosphere at room temperature for 15 hrs. Filter off the solid and concentrate the filtrate under reduced pressure. Purify the residue with flash chromatography (silica gel, EtOAc:PE=1:5) to afford the desired product (1.3 g, 73%). MS: (M+23): 262.0.

Workup

  1. filtrationFilter off the solid
  2. concentrationconcentrate the filtrate under reduced pressure
  3. customPurify the residue with flash chromatography (silica gel, EtOAc:PE=1:5)

Sources & evidence

ORD record
ord-ef311f5d17df41ff838e414a251bdca7
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

Loading…