Dimethyl malonate → Dimethyl (2-chloro-4,6-dinitrophenyl)malonate

HRID 426003Notes

Reaction equation

HRID 426003 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:11])[CH2:6][C:7]([O:9][CH3:10])=[O:8].[Cl:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([N+:22]([O-:24])=[O:23])[C:14]=1Cl>CN(C=O)C>[Cl:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([N+:22]([O-:24])=[O:23])[C:14]=1[CH:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([O:4][CH3:3])=[O:11]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 110209011,2-Dichloro-3,5-dinitrobenzene

Product 1

HCID 86634342Dimethyl (2-chloro-4,6-dinitrophenyl)malonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride was added under ice-cooling to a DMF solution of malonic acid dimethyl ester, and then 1,2-dichloro-3,5-dinitrobenzene was added thereto and allowed to undergo the reaction at room temperature overnight. By post-treating the reaction liquid, dimethyl (2-chloro-4,6-dinitrophenyl)malonate (Dat, FN: 332) was obtained. This was dissolved in DMSO, lithium chloride and water were added, followed by stirring at 100° C. for 2 hours. By post-treating the reaction liquid, methyl (2-chloro-4,6-dinitrophenyl)acetate was obtained.

Workup

  1. customthe reaction at room temperature overnight
  2. additionBy post-treating
  3. customthe reaction liquid

Sources & evidence

ORD record
ord-b41bd8129b5f41ca944a1dc041473815
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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