Bromine → N-(4-bromo-3,5-dichlorophenyl)acetamide

HRID 1018796Notes

Reaction equation

HRID 1018796 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:5]=[C:6]([NH:11][C:12](=[O:14])[CH3:13])[CH:7]=[C:8]([Cl:10])[CH:9]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Br:1][C:9]1[C:4]([Cl:3])=[CH:5][C:6]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][C:8]=1[Cl:10]

Participants

5

Reactant 3

HCID 24408BromineHCID 182054Acetamide, N-(3,5-dichlorophenyl)-HCID 517045Sodium Acetate

Product 1

HCID 18402478N-(4-bromo-3,5-dichlorophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
50 °C

Procedure

21.3 ml of bromine diluted in 82 ml of acetic acid are added over 6 hours to 84.86 g of N-(3,5-dichlorophenyl)acetamide and 34 g of sodium acetate in 420 ml of acetic acid. After 12 hours at room temperature, the reaction mixture is heated for 5 hours at 50° C. The solvents are evaporated off under reduced pressure. The residue obtained is recrystallized from isopropanol; m.p.=224° C.

Workup

  1. customThe solvents are evaporated off under reduced pressure
  2. customThe residue obtained
  3. customis recrystallized from isopropanol

Sources & evidence

ORD record
ord-4b3540b26be34f8fafeab95b115d5ad6
Source dataset
uspto-grants-2002_11
Patent number
US06482986B1

Reaction notes

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