1,3-Cyclohexanedione → 3-Oxo-1-cyclohexenyl 2,4-dibromo-3-(ethylcarbonylmethoxy)benzoate

HRID 585327Notes

Reaction equation

HRID 585327 reaction equation
[Br:1][C:2]1[C:10]([O:11][CH2:12][C:13]([CH2:15][CH3:16])=[O:14])=[C:9]([Br:17])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:18]1(=O)[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[CH2:19]1.Cl.CN(C)CCCN=C=NCC.CN(C1C=CC=CN=1)C>C(Cl)Cl>[Br:1][C:2]1[C:10]([O:11][CH2:12][C:13]([CH2:15][CH3:16])=[O:14])=[C:9]([Br:17])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:18]1[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[CH:19]=1)=[O:5]

Participants

6

Reactant 4

HCID 104341,3-CyclohexanedioneHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 223406262,4-Dibromo-3-(ethylcarbonylmethoxy)benzoic acid

Product 1

HCID 223406273-Oxo-1-cyclohexenyl 2,4-dibromo-3-(ethylcarbonylmethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.415 g (1.10 mmol) of 2,4-dibromo-3-(ethylcarbonylmethoxy)benzoic acid, 0.140 g (1.20 mmol) of cyclohexane-1,3-dione, 0.222 g (1.10 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and 0.001 g of dimethylaminopyridine were stirred in 30 ml of CH2Cl2 at room temperature for 3 h. The mixture was then diluted with CH2Cl2 and washed with 0.5 N HCl, with water, with saturated NaHCO3 solution and again with water. The combined organic phases were dried over Na2SO4 and evaporated to dryness, giving 3-oxo-1-cyclohexenyl 2,4-dibromo-3-(ethylcarbonylmethoxy)benzoate in the form of a yellow resin which was sufficiently pure for the subsequent reaction.

Workup

  1. washwashed with 0.5 N HCl, with water, with saturated NaHCO3 solution and again with water
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-93d92e08c7694bdf9985fa42dbf355bd
Source dataset
uspto-grants-2005_08
Patent number
US06930208B2

Reaction notes

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