N-bromobutanimide → N-(4-bromophenyl)-N-(2,4-dimethylphenyl)-2,4-dimethylaniline

HRID 1776076Notes

Reaction equation

HRID 1776076 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[CH3:17].C1C(=O)N([Br:31])C(=O)C1>ClCCl.[Cl-].[Na+].O>[Br:31][C:21]1[CH:22]=[CH:23][C:18]([N:9]([C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])[C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=2[CH3:17])=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 86720787N-(2,4-dimethylphenyl)-2,4-dimethyl-N-phenylaniline2×

Product 1

HCID 85826616N-(4-bromophenyl)-N-(2,4-dimethylphenyl)-2,4-dimethylanilineYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of N-(2,4-dimethylphenyl)-2,4-dimethyl-N-phenylaniline (Compound 15) (12.4 g, 41 mmol) in dichloromethane (200 mL), was added NBS (8.01 g, 45 mmol) at 0° C. The whole was stirred for about 3 hours and worked up with brine. The organic phase was dried over Na2SO4, loaded on silica gel and purified by flash column using eluents of hexanes. After removal of solvents, a colorless oil (Compound 16) was obtained (15 g, in 96% yield).

Workup

  1. dry with materialThe organic phase was dried over Na2SO4
  2. custompurified by flash column
  3. customAfter removal of solvents

Sources & evidence

ORD record
ord-fe09e9c728ba4185995deb4b01e923ff
Source dataset
uspto-grants-2016_02
Patent number
US09263681B2

Reaction notes

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