Dimethylformamide → 4-bromo-N-(3,5-dimethylbenzyl)aniline

HRID 1363646Notes

Reaction equation

HRID 1363646 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[CH2:5]Br.[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][CH2:5][C:4]2[CH:3]=[C:2]([CH3:1])[CH:9]=[C:8]([CH3:10])[CH:7]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78074-BromoanilineHCID 11430Potassium CarbonateHCID 1413343,5-Dimethylbenzyl bromide

Product 1

HCID 598208394-bromo-N-(3,5-dimethylbenzyl)anilineYield 90.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,5-dimethylbenzyl bromide (1.59 g, 7.986 mmol), 4-bromoaniline (1.374 g, 7.986 mmol), potassium carbonate (5.519 g, 39.93 mmol) and N,N-dimethylformamide (6.5 ml) was stirred at 80° for 2 hours under argon atmosphere. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=15:1) to give the title compound (2.106 g, 57.2%) as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained by evaporation of the solvent under reduced pressure
  5. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-338dcf427ecc4733aaf42edd414a9f69
Source dataset
uspto-grants-2011_02
Patent number
US07884234B2

Reaction notes

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