1-Chloro-4-nitrobenzene → Diethyl 2-(4-nitrophenyl)malonate

HRID 1898903Notes

Reaction equation

HRID 1898903 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CC(C)([O-])C.[K+].Cl[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>CS(C)=O>[N+:25]([C:22]1[CH:23]=[CH:24][C:19]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[CH:20][CH:21]=1)([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 7761Diethyl MalonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 10869708Diethyl 2-(4-nitrophenyl)malonate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
100 °C

Procedure

12.0 g (74.9 mmol) diethyl malonate were dissolved in 50 ml DMSO and 8.6 g (76.6 mmol) potassium t-butoxide were added. A solution of 7.9 g (50.1 mmol) 1-chloro-4-nitrobenzene in 50 ml DMSO was added via a dropping funnel. The mixture was heated at 100° C. for 4 h and poured on to crushed ice. It was extracted twice with ethyl acetate, the combined organic layers washed with brine, dried over sodium sulfate, and evaporated in vacuo to afford a brown oil, which contained the title compound in an amount of about 75% and which was used in the reaction of the next step.

Workup

  1. additionpoured on
  2. customto crushed ice
  3. extractionIt was extracted twice with ethyl acetate
  4. washthe combined organic layers washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customto afford a brown oil, which

Sources & evidence

ORD record
ord-4165a9870e1446eda0c995916f09768b
Source dataset
uspto-grants-1996_11
Patent number
US05571813

Reaction notes

Loading…