Dimethyl malonate → HCID 57457659, compound

HRID 551087Notes

Reaction equation

HRID 551087 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].CC(C)([O-])C.[K+].Cl[C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20]([F:26])=[CH:19][C:18]=1[N+:27]([O-:29])=[O:28].[NH4+].[Cl-]>CC(N(C)C)=O.O1CCOCC1>[F:26][C:20]1[CH:21]=[C:22]([N+:23]([O-:25])=[O:24])[C:17]([CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[C:18]([N+:27]([O-:29])=[O:28])[CH:19]=1

Participants

7

Reactant 4

HCID 7943Dimethyl malonateHCID 25517Ammonium ChlorideHCID 123611032-Chloro-5-fluoro-1,3-dinitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 57457659HCID 57457659, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of dimethyl malonate (16.3 mL, 143 mmol) in DMA (100 mL) at ambient temperature was added potassium tert-butoxide (15.3 g, 136 mmol). The reaction mixture was heated to 70° C. for 30 min, then removed from the oil bath. A solution of 2-chloro-5-fluoro-1,3-dinitrobenzene (14.3 g, 64.9 mmol) in dioxane (70 mL) was added drop wise over 30 min. The reaction mixture was stirred for 10 min, then cooled and poured onto saturated aqueous NH4Cl (500 mL). The aqueous layer was extracted with EtOAc (250 mL) and Et2O (2×250 mL). The combined organic extracts were washed with H2O (100 mL), dried over Na2SO4, and concentrated in vacuo to give the title compound, which was used without further purification. MS: m/z=317 (M+1).

Workup

  1. customremoved from the oil bath
  2. temperaturecooled
  3. extractionThe aqueous layer was extracted with EtOAc (250 mL) and Et2O (2×250 mL)
  4. washThe combined organic extracts were washed with H2O (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3bfca5722934db99d63c7f159a06f5a
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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