N-bromobutanimide → 2-Bromo-4-chloro-6-methoxy-3-methylaniline

HRID 1710819Notes

Reaction equation

HRID 1710819 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:16]([CH3:17])=[CH:15][C:13]([NH2:14])=[C:12]([O:18][CH3:19])[CH:11]=1>C(#N)C>[Br:1][C:15]1[C:16]([CH3:17])=[C:10]([Cl:9])[CH:11]=[C:12]([O:18][CH3:19])[C:13]=1[NH2:14]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 807824-Chloro-5-methyl-o-anisidine

Product 1

HCID 714278142-Bromo-4-chloro-6-methoxy-3-methylanilineYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Bromosuccinimid (3.9 g, 22 mmol) was added to 4-chloro-2-methoxy-5-methylanilin (4.04 g, 20 mmol) dissolved in acetonitril (200 ml). The reaction was stirred at r.t. overnight, and the solvent was evaporated. The residue was purified by column chromatography (silica gel, methylene chloride) to yield the title compound (3.1 g, 62%) as an orange solid.

Workup

  1. customthe solvent was evaporated
  2. customThe residue was purified by column chromatography (silica gel, methylene chloride)

Sources & evidence

ORD record
ord-c7aa83a95d964f048c8c3b263b292300
Source dataset
uspto-grants-2010_09
Patent number
US07790733B2

Reaction notes

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