Dimethyl malonate → Dimethyl 2-(4-bromobenzyl)malonate

HRID 566506Notes

Reaction equation

HRID 566506 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Br)=[CH:13][CH:12]=1.[H-].[Na+]>CN(C=O)C>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromide

Product 1

HCID 2801290Dimethyl 2-(4-bromobenzyl)malonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of dimethyl malonate (13.2 g), 4-bromobenzylbromide (5.4 g) in DMF (200 mL) was treated with NaH (4 g, 60% in mineral oil). The mixture was stirred for 5 min at 0° C. and 20 min at room temperature and then quenched with 10 mL of AcOH slowly. The mixture was concentrated under vacuum and the residue was dissolved in 200 mL of 1:1 EtOAc/hexane, and filtered through a pad of silica gel. The filtrate was concentrated and the excess dimethyl malonate was removed under vacuum at 70° C. to provide the title compound as a yellow oil.

Workup

  1. customquenched with 10 mL of AcOH slowly
  2. concentrationThe mixture was concentrated under vacuum
  3. dissolutionthe residue was dissolved in 200 mL of 1:1 EtOAc/hexane
  4. filtrationfiltered through a pad of silica gel
  5. concentrationThe filtrate was concentrated
  6. customthe excess dimethyl malonate was removed under vacuum at 70° C.

Sources & evidence

ORD record
ord-67d32fd4c5a649d69e0ebaf461322608
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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