Diethyl ethylmalonate → Diethyl 2-(2-bromobenzyl)-2-methylmalonate

HRID 1585971Notes

Reaction equation

HRID 1585971 reaction equation
[OH-].[Na+].[CH2:3]([CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[Br:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19]Br>C1(C)C=CC=CC=1>[Br:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][C:5]([CH3:3])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 8610Diethyl ethylmalonateHCID 14798Sodium HydroxideHCID 769652-Bromobenzyl bromide

Product 1

HCID 21217385Diethyl 2-(2-bromobenzyl)-2-methylmalonateYield 109.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

In a reaction vessel purged with nitrogen was weighed 14.0 g of sodium hydroxide (349 mmole), and suspended in 200 ml of toluene, to which 100 ml of a toluene solution of diethyl ethylmalonate (60.0 ml, 320 mmole) was added dropwise in an ice bath. After the addition was completed and the mixture was stirred at room temperature for 3 hours, 100 ml of a toluene solution of 2-bromobenzyl bromide (80.0 g, 320 mmole) was added dropwise, and the mixture was stirred overnight. The reaction was terminated by pouring the reaction mixture to dilute hydrochloric acid, and the organic layer was washed with water, dried and concentrated to give 120 g of diethyl 2-(2-bromobenzyl)-2-methylmalonate as a yellow oil (yield, 100%).

Workup

  1. customIn a reaction vessel purged with nitrogen
  2. additionwas added dropwise in an ice bath
  3. additionAfter the addition
  4. stirringthe mixture was stirred overnight
  5. customThe reaction was terminated
  6. additionby pouring the reaction mixture to dilute hydrochloric acid
  7. washthe organic layer was washed with water
  8. customdried
  9. concentrationconcentrated
  10. customto give

Sources & evidence

ORD record
ord-f9bb8c3cdf414dabaf5d88f6fc4a837f
Source dataset
uspto-grants-1999_08
Patent number
US05942459

Reaction notes

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