Water → N-isopropyl-4'-chloro-4-bromo-2-methylacetoacetanilide

HRID 224499Notes

Reaction equation

HRID 224499 reaction equation
[CH:1]([N:4]([C:12](=[O:18])[CH:13]([CH3:17])[C:14]([CH3:16])=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[Br:19]Br.O>C(O)(=O)C>[CH:1]([N:4]([C:12](=[O:18])[CH:13]([CH3:17])[C:14]([CH2:16][Br:19])=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 20297522N-isopropyl-4'-chloro-2-methylacetoacetanilide

Product 1

HCID 20297527N-isopropyl-4'-chloro-4-bromo-2-methylacetoacetanilideYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a reaction flask which contained 71.6 g (0.267 mole) of N-isopropyl-4'-chloro-2-methylacetoacetanilide dissolved in 360 ml of glacial acetic acid, there was added dropwise a solution of 42.7 g (0.267 mole) of bromine in 30 ml of acetic acid. The solution was stirred overnight at ambient temperature. On the following morning, the reaction solution was added to two liters of cold water and the organic material was extracted into toluene. The latter was washed with water and dried over sodium sulfate. After removal of the solvent, there was obtained 86.6 g (97%) of residual oil. N.M.R. (CDCl3) ∂0.9-1.4 (CH3, 9 protons), 3.3-3.6 (CH), 3.9-4.0 (CH2Br), 4.8-5.2 (CH, isopropyl), 7.1-7.6 (aromatic).

Workup

  1. customTo a reaction flask which contained
  2. extractionthe organic material was extracted into toluene
  3. washThe latter was washed with water
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of the solvent

Sources & evidence

ORD record
ord-c38bb847a3a6452ea265670805da1e3c
Source dataset
uspto-grants-1980_11
Patent number
US04232163

Reaction notes

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