Aniline → 2-Bromo-4-methylaniline

HRID 1886239Notes

Reaction equation

HRID 1886239 reaction equation
NC1C=CC=CC=1.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.[Br-:16].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.FC1C=CC(N)=CC=1>>[Br:16][C:10]1[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=1[NH2:8]

Participants

5

Reactant 4

HCID 6115AnilineHCID 7813p-ToluidineHCID 97314-FluoroanilineHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 114222-Bromo-4-methylanilineYield 66%

Procedure

To show that selectivity is still obtained using a highly activated aniline, bromination of p-toluidine using tetrabutylammonium tribromide was carried out as generally described in Example 4, but substituting p-toluidine for 4-fluoroaniline, on a 0.75 mole reaction. The desired product 2-bromo-4-methylaniline was obtained in 66% yield on the 0.75 mole reaction.

Workup

  1. customis still obtained
  2. customon a 0.75 mole reaction

Sources & evidence

ORD record
ord-b8db115abbb14141ae693861e738ef4f
Source dataset
uspto-grants-1992_09
Patent number
US05149875

Reaction notes

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