Sodium Chloride → HCID 67276324, compound

HRID 1698412Notes

Reaction equation

HRID 1698412 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=1.[Cl-].[Na+]>CN(C=O)C>[Br:9][C:10]1[CH:15]=[C:14]([Cl:1])[C:13]([NH2:16])=[C:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 31398ChlorosuccinimideHCID 119590004-bromo-2-tert-butylphenylamine

Product 1

HCID 67276324HCID 67276324, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

6.4 g (48 mmol) of N-chlorosuccinimide are added to a solution of 10 g (44 mmol) of 4-bromo-2-tert-butylphenylamine (example 1a) in 150 ml of DMF. The medium is heated at 70° C. for 2 hours. It is then poured into a saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The organic phases are combined and washed with water and then dried over sodium sulphate. The residue is chromatographed on silica gel (90/10 heptane/ethyl acetate). 11.4 g of 4-bromo-2-tert-butyl-6-chlorophenylamine are obtained in the form of an orange oil (yield=99%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over sodium sulphate
  4. customThe residue is chromatographed on silica gel (90/10 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-9d00c41e144640ff8c9e2c3a52dc7fcc
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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