Dimethyl malonate → Dimethyl (4-Fluorobenzyl)Malonate

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

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.