2-Bromo-1-chloro-4-nitrobenzene → 3-Bromo-4-chloroaniline

HRID 2261261Notes

Reaction equation

HRID 2261261 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[Cl:11]>[Pd].CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[Cl:11]

Participants

4

Reactant 1

HCID 27355492-Bromo-1-chloro-4-nitrobenzene

Product 1

HCID 128437223-Bromo-4-chloroaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-bromo-1-chloro-4-nitrobenzene (1.57 g, 6.6 mmol) and 10% palladium on charcoal (297 mg, 2.8 mmol) in EtOAc (50 mL) was stirred under an atmosphere of hydrogen (balloon) for 4 h. The reaction mixture was filtered through a pad of celite washing with EtOAc. The EtOAc was removed under reduced pressure affording the title compound as brown oil which solidified upon standing. It was used in the next step without further purification. MS (ESI, pos.ion) m/z: 206.0/208.0 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwashing with EtOAc
  3. customThe EtOAc was removed under reduced pressure

Sources & evidence

ORD record
ord-af096638cc4d40a188eb2aecb2eed5bf
Source dataset
uspto-grants-2010_12
Patent number
US07846944B2

Reaction notes

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