Chlorosuccinimide → 1-(2-Amino-5-bromo-3-chlorophenyl)ethanone

HRID 1880378Notes

Reaction equation

HRID 1880378 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[Cl:12]N1C(=O)CCC1=O>C(Cl)Cl>[NH2:1][C:2]1[C:7]([Cl:12])=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 110747461-(2-Amino-5-bromophenyl)ethan-1-one

Product 1

HCID 669204111-(2-Amino-5-bromo-3-chlorophenyl)ethanoneYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-amino-5-bromophenyl)ethanone (200 mg, 0.93 mmol) in CH2Cl2 (5 mL) was added N-chlorosuccinimide (125 mg, 0.93 mmol). The mixture was stirred at room temperature overnight. Analysis indicated that the reaction was incomplete; therefore, additional N-chlorosuccinimide (125 mg, 0.93 mmol) was added and the mixture was stirred at room temperature overnight. The solvents were removed under reduced pressure and the residue was purified by CombiFlash (40 g column, 0-10% EtOAc/heptane) to afford 1-(2-amino-5-bromo-3-chlorophenyl)ethanone (206 mg, 89%).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was purified by CombiFlash (40 g column, 0-10% EtOAc/heptane)

Sources & evidence

ORD record
ord-2a9c91df13614deea504ccdadffb74a3
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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