Potassium Carbonate → Butyl-a-bromoacrylate

HRID 1648976

Reaction equation

HRID 1648976 reaction equation
[Br:1][CH:2]([CH2:10]Br)[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4].C(=O)([O-])[O-].[K+].[K+]>COC1C=CC(O)=CC=1.C(#N)C>[Br:1][C:2](=[CH2:10])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 519844Propanoic acid, 2,3-dibromo-, butyl ester

Product 1

HCID 19901948Butyl-a-bromoacrylateYield 90.9%

Reagents, catalysts & solvents 2

HCID 90154-MethoxyphenolCatalystHCID 6342AcetonitrileSolvent

Procedure

The product (300 g) of Step 1 and p-methoxyphenol (2 g) was added to a 2 l. round bottom flask fitted with a thermometer, condenser, stirrer and inlet for nitrogen, and containing acetonitrile (1000 ml) and anhydrous potassium carbonate (330 g). The reaction mixture was stirred under reflux for 8 hours and cooled, and the salts were filtered off. The filtrate was evaporated under reduced pressure to remove the solvent, and the residue was dissolved in dichloromethane. The solution was dried (Na2SO4), filtered and evaporated. Distillation of the residue afforded n-butyl 2-bromoacrylate (196 g; 90%), b.p. 90°/15 mmHg.

Workup

  1. customround bottom flask fitted with a thermometer, condenser, stirrer and inlet for nitrogen
  2. temperatureunder reflux for 8 hours
  3. temperaturecooled
  4. filtrationthe salts were filtered off
  5. customThe filtrate was evaporated under reduced pressure
  6. customto remove the solvent
  7. dissolutionthe residue was dissolved in dichloromethane
  8. dry with materialThe solution was dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. distillationDistillation of the residue

Sources & evidence

ORD record
ord-1b01719e826d4861abd8b95da613c813
Source dataset
uspto-grants-1983_11
Patent number
US04414391

Linked notes

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