Sodium Chloride → 4-Bromo-2-ethyl-6-methylaniline

HRID 1880418Notes

Reaction equation

HRID 1880418 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:4]=1[NH2:5])[CH3:2].[Br:11]N1C(=O)CCC1=O.[Na+].[Cl-]>CN(C=O)C>[Br:11][C:8]1[CH:7]=[C:6]([CH3:10])[C:4]([NH2:5])=[C:3]([CH2:1][CH3:2])[CH:9]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 324852-Ethyl-6-methylanilineHCID 67184N-bromobutanimide

Product 1

HCID 9607614-Bromo-2-ethyl-6-methylanilineYield 100.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-ethyl-6-methylaniline (2.03 g, 15 mmol) in DMF (50 mL) at 0° C. was added N-bromosuccinimide (2.66 g, 14.9 mmol). The mixture was stirred at room temperature for 10 minutes before addition to saturated aqueous NaCl. The mixture was extracted with EtOAc, the organic phase was washed with sat aqueous NaCl (2×), concentrated and the crude material was purified by Biotage chromatography (40M, 15% EtOAc/heptane) to provide 4-bromo-2-ethyl-6-methylbenzenamine as a red brown liquid (3.21 g, 100%).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe organic phase was washed with sat aqueous NaCl (2×)
  3. concentrationconcentrated
  4. customthe crude material was purified by Biotage chromatography (40M, 15% EtOAc/heptane)

Sources & evidence

ORD record
ord-56f1cd15f4c445589cf0869e45f331a0
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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