Pyridine → 5-Bromo-6-methyl-1,3-benzodioxole

HRID 1835403Notes

Reaction equation

HRID 1835403 reaction equation
[Br:1]Br.[CH2:3]1[O:11][C:10]2[CH:9]=[CH:8][C:7]([CH3:12])=[CH:6][C:5]=2[O:4]1.N1C=CC=CC=1>ClCCl>[Br:1][C:8]1[CH:9]=[C:10]2[O:11][CH2:3][O:4][C:5]2=[CH:6][C:7]=1[CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 815641,3-Benzodioxole, 5-methyl-

Product 1

HCID 787285-Bromo-6-methyl-1,3-benzodioxoleYield 104.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.2 ml (62 mmol) of bromine was dropwise added at 0° C. to a solution having 7.0 ml (58 mmol) of 3,4-(methylenedioxy)toluene and 5.5 ml (68 mmol) of pyridine dissolved in 110 ml of dichloromethane, followed by stirring for 30 minutes, and the temperature was raised to room temperature, followed by stirring for 22 hours. The mixture was washed with an aqueous sodium hydroxide solution, dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 13 g (yield 99%) of 2-bromo-4,5-(methylenedioxy)toluene.

Workup

  1. stirringby stirring for 22 hours
  2. washThe mixture was washed with an aqueous sodium hydroxide solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationsubjected to filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe crude product thus obtained
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-617b810d840f40c8b26fb54665c2d80d
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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