Dimethyl malonate → Dimethyl bromomalonate

HRID 2088326Notes

Reaction equation

HRID 2088326 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:13]N1C(=O)CCC1=O.[C:21]([O:28][CH3:29])(=[O:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24]>C(OC(=O)C)C.CCCCCC>[CH3:26][O:25][C:23](=[O:24])[CH:22]([Br:13])[C:21]([O:28][CH3:29])=[O:27]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 67184N-bromobutanimideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 70087Dimethyl bromomalonate

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

p-Toluene sulfonic acid monohydrate (11.0 g, 0.057 mol) and N-bromosuccinimide (1.74 g, 0.009 mol) were slowly added to a stirred solution of dimethyl malonate (5.0 g, 0.037 mol) in CH3CH (30 mL). The resulting mixture was heated at reflux for 2 hours, evaporated and dissolved in dichloromethane. The organic layer was washed with H2O, dried over MgSO4 and concentrated. An analytically pure sample was to obtained by column chromatography on silica gel using a 1:4 mixture of ethylacetate/hexane. Yield: 6.0 g (76.0%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. customevaporated
  4. dissolutiondissolved in dichloromethane
  5. washThe organic layer was washed with H2O
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto obtained by column chromatography on silica gel using

Sources & evidence

ORD record
ord-a588caf709c04cd4bad1c37d35c20e76
Source dataset
uspto-grants-2013_05
Patent number
US08435931B2

Reaction notes

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