Hydrogen Bromide → HCID 10827115, compound

HRID 466967Notes

Reaction equation

HRID 466967 reaction equation
N([O-])=O.[Na+].[CH2:5]1[O:14][C:13]2[CH:12]=[CH:11][C:9](N)=[CH:8][C:7]=2[O:6]1.[BrH:15].[C:16]([O:20][CH3:21])(=[O:19])[CH:17]=[CH2:18]>O.CC(C)=O>[Br:15][CH:17]([CH2:18][C:9]1[CH:11]=[CH:12][C:13]2[O:14][CH2:5][O:6][C:7]=2[CH:8]=1)[C:16]([O:20][CH3:21])=[O:19]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 7294Methyl AcrylateHCID 843101,3-Benzodioxol-5-amineHCID 23668193Sodium Nitrite

Product 1

HCID 10827115HCID 10827115, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A solution of sodium nitrite (27.7 g) in water (40.0 ml) was added dropwise to a mixture of 3,4-methylenedioxyaniline (50 g), aq. HBr (47%, 125 ml) and acetone (500 ml) at 0°-5° C., followed by stirring for 20 minutes at 5° C. To the solution was added methyl acrylate (197 ml). The resultant solution was warmed to 32° C. to which cuprous oxide (Cu2O) (0.5 g) was added in small portions with vigorous stirring. The mixture generates nitrogen gas due to exothermic reaction. After completing the generation of nitrogen gas, the reaction mixture was further stirred for an hour and concentrated under reduced pressure. Water was poured into the reaction mixture and the mixture was extracted with ether. The ethereal layer was washed with H2O, dried (MgSO4) and distilled off under reduced pressure to give methyl 2-bromo-3-(3,4methylenedioxyphenyl)propionate (56.2 g, 54%).

Workup

  1. additionwas added in small portions with vigorous stirring
  2. customdue to exothermic reaction
  3. stirringthe reaction mixture was further stirred for an hour
  4. concentrationconcentrated under reduced pressure
  5. additionWater was poured into the reaction mixture
  6. extractionthe mixture was extracted with ether
  7. washThe ethereal layer was washed with H2O
  8. dry with materialdried (MgSO4)
  9. distillationdistilled off under reduced pressure

Sources & evidence

ORD record
ord-f13160b08e234253ae30714a9912740a
Source dataset
uspto-grants-1992_10
Patent number
US05158943

Reaction notes

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