Iodine → 4-Bromo-3-oxo-n-phenylbutanamide

HRID 231126

Reaction equation

HRID 231126 reaction equation
[Br:1]Br.II.[C:5]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:10])[CH2:6][C:7]([CH3:9])=[O:8].O>C(O)(=O)C>[Br:1][CH2:9][C:7](=[O:8])[CH2:6][C:5]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10]

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 7592AcetoacetanilideHCID 24408Bromine

Product 1

HCID 2682684-Bromo-3-oxo-n-phenylbutanamideYield 57.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Under a nitrogen atmosphere, a solution of bromine (1.16 ml, 22.59 mmol) in 17 ml of acetic acid containing a small crystal of iodine was added over 2.5 hours to a solution of acetoacetanilide (4.0 g, 22.57 mmol) in 12 ml of acetic acid, at room temperature (cooling with cold water). The reaction mixture was stirred at room temperature for 3 hours, then poured into 100 ml of ice-cold water and the crude solid product was filtered off. Following crystallization from ethanol, 3.30 g of 4-bromoacetoacetanilide were obtained, m.p 130°-132° C.

Workup

  1. filtrationthe crude solid product was filtered off
  2. customcrystallization from ethanol

Sources & evidence

ORD record
ord-45b4fc509abb4490ad526c6f3f0b3c90
Source dataset
uspto-grants-1989_07
Patent number
US04845122

Linked notes

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