1-Bromo-4-(methylsulphonyl)benzene → 2-Methyl-5-(phenylsulfonyl)aniline

HRID 2390197Notes

Reaction equation

HRID 2390197 reaction equation
CS(C1C=CC(CCC)=C(C=1)N)(=O)=O.[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])=[CH:18][C:17]=1[N+:31]([O-])=O.CS(C1C=CC(Br)=CC=1)(=O)=O>CO.CCOC(C)=O>[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)(=[O:24])=[O:23])=[CH:18][C:17]=1[NH2:31]

Participants

6

Reactant 3

HCID 770141-Bromo-4-(methylsulphonyl)benzeneHCID 565939761-Methyl-2-nitro-4-(phenylsulfonyl)benzene2×HCID 585220065-(Methylsulfonyl)-2-propylaniline

Product 1

HCID 215554692-Methyl-5-(phenylsulfonyl)anilineYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following the general method as outlined in Intermediate 61 using MeOH and EtOAc as solvents, starting from 1-methyl-2-nitro-4-(phenylsulfonyl)benzene (Intermediate 112) and 4-bromophenyl methyl sulfone, the title compound was obtained as a beige solid in 94% yield.

Sources & evidence

ORD record
ord-ef3929842697450580ce7764d3b6a8f4
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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