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Methyl iodide → Dimethyl 2-(2-fluoro-4-nitrophenyl)-2-methylmalonate

HRID 1842963
Notes
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Reaction equation

HRID 1842963 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH:11]([C:16]([O:18][CH3:19])=[O:17])[C:12]([O:14][CH3:15])=[O:13].[C:20]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([CH3:20])([C:16]([O:18][CH3:19])=[O:17])[C:12]([O:14][CH3:15])=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 53429620Dimethyl 2-(2-fluoro-4-nitrophenyl)malonate

Product 1

HCID 70816610Dimethyl 2-(2-fluoro-4-nitrophenyl)-2-methylmalonateYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of dimethyl 2-(2-fluoro-4-nitrophenyl)malonate (200 mg, 0.73 mmol, 1.0 eq) and K2CO3 (204 mg 1.47 mmol 2.0 eq) in DMF (5 mL), was added methyl iodide (210 mg, 1.47 mmol 2.0 eq) at RT and the mixture was stirred at RT for 6 h. K2CO3 was filtered out and the filtrate concentrated under vacuum. The residue was diluted with water (50 mL) and extracted with EtOAc (20 mL). The organic layer was separated washed with brine solution, dried over anhydrous Na2SO4 and the solvent evaporated to get dimethyl 2-(2-fluoro-4-nitrophenyl)-2-methylmalonate (150 mg, 71%; TLC system: EtOAc/PE (1:9), Rf: 0.4).

Workup

  1. filtrationK2CO3 was filtered out
  2. concentrationthe filtrate concentrated under vacuum
  3. additionThe residue was diluted with water (50 mL)
  4. extractionextracted with EtOAc (20 mL)
  5. customThe organic layer was separated
  6. washwashed with brine solution
  7. dry with materialdried over anhydrous Na2SO4
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-f4751ed8c1d643cda2eac8ddcf0f13e9
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946204B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes