N-bromobutanimide → HCID 18989155, compound

HRID 2395567Notes

Reaction equation

HRID 2395567 reaction equation
[CH3:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18989142HCID 18989142, compound

Product 1

HCID 18989155HCID 18989155, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of methyl 4-methyl-1,3-benzodioxole-5-carboxylate (9.9 g), N-bromosuccinimide (9.6 g) in carbon tetrachloride was irradiated with a 500 W medium pressure ultraviolet lamp for six hours at reflux. The mixture was cooled to 0° C., filtered and the filtrate evaporated to give an oil which was crystallised from toluene/hexane and recrystallised from cyclohexane to give methyl 4-bromomethyl-1,3-benzodioxole-5-carboxylate (3.0 g) as a beige solid, m.p. 95°.varies.98° C.

Workup

  1. customwas irradiated with a 500 W medium pressure ultraviolet lamp for six hours
  2. temperatureat reflux
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. customto give an oil which
  6. customwas crystallised from toluene/hexane
  7. customrecrystallised from cyclohexane

Sources & evidence

ORD record
ord-20270a6291de4b5f8dfcfdecd66fb821
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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