Diethyl Malonate → Diethyl 2-(2-bromobenzyl)malonate

HRID 255993

Reaction equation

HRID 255993 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Na].[Br:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Br.[Br-].[Na+]>C(O)C>[Br:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 769652-Bromobenzyl bromideHCID 253881Sodium BromideHCID 5360545Sodium

Product 1

HCID 12853296Diethyl 2-(2-bromobenzyl)malonateYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl malonate (77 g, 0.48 mol) was added to a stirred solution of sodium (10.2 g, 0.425 mol) in ethanol (800 ml) followed by 2-bromobenzyl bromide (100 g, 0.40 mol). Sodium bromide began to separate towards the end of the addition and the mixture became warm. The reaction was completed by refluxing on a steam bath for 3 hours and then cooling overnight. The bulk of the solvent was removed in vacuo, water was added and the product extracted into ether. After drying (CaCl2) and evaporation the product was distilled to give 93.28 g (71%) of material of bp0.2 130° C. (lit bp0.004 115°-120° C., F. G. Holliman and F. G. Mann J. Chem. Soc. 9, [1960]).

Workup

  1. customto separate towards the end of the addition
  2. temperaturethe mixture became warm
  3. temperatureby refluxing on a steam bath for 3 hours
  4. temperaturecooling overnight
  5. customThe bulk of the solvent was removed in vacuo, water
  6. additionwas added
  7. extractionthe product extracted into ether
  8. customAfter drying
  9. custom(CaCl2) and evaporation the product
  10. distillationwas distilled

Sources & evidence

ORD record
ord-37e19e9937584beea98ab370d4bf0d4b
Source dataset
uspto-grants-1987_10
Patent number
US04699995

Linked notes

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