Dimethyl malonate → Dimethyl (4-Fluorobenzyl)Malonate

HRID 1795183Notes

Reaction equation

HRID 1795183 reaction equation
[Na].[C:2]([O:9][CH3:10])(=[O:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1>CO>[CH3:7][O:6][C:4](=[O:5])[CH:3]([CH2:16][C:15]1[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=1)[C:2]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 680214-Fluorobenzyl bromideHCID 5360545Sodium

Product 1

HCID 2781576Dimethyl (4-Fluorobenzyl)Malonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of anhydrous methanol (250 mL) is added sodium metal (2.875 g, 0.125 mol) piecewise until the evolution of gas has deceased. Dimethyl malonate (16.5 g, 0.125 mol) is added dropwise and the mixture is stirred for 30 minutes. 4-Fluoro benzyl bromide (23.8 g, 0.126 mol) is added dropwise, and the reaction is refluxed for 2 hour. The majority of the solvent is removed under vacuum, and aqueous HCl is added. The solution is extracted with CHCl3, dried, and the solvent removed in vacuo. Distillation of the crude material under reduced pressure provides the desired compound which is used without further purification.

Workup

  1. temperaturethe reaction is refluxed for 2 hour
  2. customThe majority of the solvent is removed under vacuum, and aqueous HCl
  3. additionis added
  4. extractionThe solution is extracted with CHCl3
  5. customdried
  6. customthe solvent removed in vacuo
  7. distillationDistillation of the crude material under reduced pressure

Sources & evidence

ORD record
ord-21a53e0fc47143a7a0f6a6701eaaedad
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

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