Dimethylformamide → 1,3-Diethyl 2-(3-fluoro-4-nitrophenyl)-2-methylpropanedioate

HRID 434576Notes

Reaction equation

HRID 434576 reaction equation
[F:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([O:14][C:15](=[O:23])[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:13].CN(C)C=O.[OH-].[Na+]>O>[F:1][C:2]1[CH:7]=[C:6]([C:16]([CH3:22])([C:15]([O:14][CH2:12][CH3:13])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11857Diethyl methylmalonateHCID 14798Sodium HydroxideHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 42638641,3-Diethyl 2-(3-fluoro-4-nitrophenyl)-2-methylpropanedioate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 50.0 g (0.31 mol) of 2,4-difluoronitrobenzene II, 56.1 g (0.32 mol) of diethylmethylmalonate and 400 ml of dimethylformamide are vigorously stirred. To the stirring mixture is added 13.1 g (0.33 mol) sodium hydroxide in one portion at 25° C., cooling with ice to keep the temperature of the reaction mixture at 25°-30° C. during the first hour. Thereafter, stirring is maintained for 3.5 hours, then 800 ml of water is added, the organic layers removed, and the aqueous layer extracted with three 180-ml portions of ethyl acetate-water.

Workup

  1. temperaturecooling with ice
  2. customat 25°-30° C.
  3. stirringThereafter, stirring
  4. temperatureis maintained for 3.5 hours
  5. customthe organic layers removed
  6. extractionthe aqueous layer extracted with three 180-ml portions of ethyl acetate-water

Sources & evidence

ORD record
ord-e552940c5e894c0d8711e06b924b9e31
Source dataset
uspto-grants-1983_08
Patent number
US04398035

Reaction notes

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