2-[(Benzenesulfonyl)methyl]-4-bromo-1-nitrobenzene → 4-Bromo-2-[(phenylsulfonyl)methyl]benzenamine

HRID 1990968Notes

Reaction equation

HRID 1990968 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:12]=2[N+:18]([O-])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>[Ni].C(OCC)(=O)C>[Br:17][C:15]1[CH:14]=[CH:13][C:12]([NH2:18])=[C:11]([CH2:10][S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:8])=[O:9])[CH:16]=1

Participants

5

Reactant 2

HCID 124463822-[(Benzenesulfonyl)methyl]-4-bromo-1-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 290623094-Bromo-2-[(phenylsulfonyl)methyl]benzenamineYield 100.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared by catalytic hydrogenation of 5-bromo-2-nitrobenzyl phenyl sulfone (0.23 g, 0.64 mmol) in the presence of Raney nickel and hydrogen (45 psi) in ethyl acetate (30 ml) for 1 hour. The reaction mixture is filtered through celite and concentrated in vacuo to give the title compound as a light brown solid (0.21 g, 99%). Mp: 140-141° C. MS (ES+): 326 (M+H).

Workup

  1. filtrationThe reaction mixture is filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3625365b9f7d4d44bc313e00c2cd4612
Source dataset
uspto-grants-2010_01
Patent number
US07645752B2

Reaction notes

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