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Dimethyl malonate → 1,3-Dimethyl 2-(4-bromo-2-nitrophenyl)propanedioate

HRID 422032
Notes
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Reaction equation

HRID 422032 reaction equation
[H-].[Na+].[C:3]([O:10][CH3:11])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[Br:12][C:13]1[CH:18]=[CH:17][C:16](F)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1>CS(C)=O>[CH3:8][O:7][C:5](=[O:6])[CH:4]([C:16]1[CH:17]=[CH:18][C:13]([Br:12])=[CH:14][C:15]=1[N+:20]([O-:22])=[O:21])[C:3]([O:10][CH3:11])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 157405961,3-Dimethyl 2-(4-bromo-2-nitrophenyl)propanedioate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of NaH (60% in mineral oil, 972 mg, 24.3 mmol) in DMSO (16 mL) is added dimethyl malonate (2.78 mL, 24.3 mmol). The mixture is heated at 60° C. for 10 min and then is cooled to room temperature before 4-bromo-1-fluoro-2-nitro-benzene (1.0 mL, 8.1 mmol) is added. The resulting mixture is heated at 60° C. for 3 hr and then is quenched with saturated aqueous NH4Cl solution. The mixture is extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated. The crude is used without further purification.

Workup

  1. additionis added
  2. temperatureThe resulting mixture is heated at 60° C. for 3 hr
  3. customis quenched with saturated aqueous NH4Cl solution
  4. extractionThe mixture is extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe crude is used without further purification

Sources & evidence

ORD record
ord-c24f09dbbd18411d807358b383b3f8db
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08101608B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes