1-Iodo-4-nitro-2-(trifluoromethyl)benzene → 4-Iodo-3-(trifluoromethyl)aniline

HRID 1660948Notes

Reaction equation

HRID 1660948 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]>CO.[Ni]>[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

4

Reactant 1

HCID 192617781-Iodo-4-nitro-2-(trifluoromethyl)benzene

Product 1

HCID 230036244-Iodo-3-(trifluoromethyl)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-iodo-4-nitro-2-trifluoromethyl-benzene (see WO 00/09495) (0.500 g, 1.58 mmol) and Raney Ni (˜0.100 g) in MeOH (10 mL) is stirred for 2 h at rt under a hydrogen atmosphere. The reaction mixture is filtered through a pad of Celite and concentrated to afford the title compound as a brown solid: ES-MS: 285.8 []−; single peak at tR=4.49 min (System 1); Rf=0.33 (Hexane/CH2Cl2, 2:3).

Workup

  1. filtrationThe reaction mixture is filtered through a pad of Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-870b4fc816b8411f8654d6cd57c78b58
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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