1,3-Benzodioxole → 1-Bromo-3,4-(methylenedioxy)benzene

HRID 2205109Notes

Reaction equation

HRID 2205109 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH2:2]1.[Br:10]NC(=O)CCC(N)=O>C(Cl)(Cl)Cl>[Br:10][C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1

Participants

4

Reactant 2

HCID 92291,3-BenzodioxoleHCID 9834204N-Bromosuccinamide

Product 1

HCID 758311-Bromo-3,4-(methylenedioxy)benzeneYield 94.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of benzo[d][1,3]dioxole (6.1 g, 50.00 mmol, 1.00 equiv) and N-bromo-succinamide (NBS) (9.3 g, 52.5 mmol, 1.05 equiv) in CHCl3 (25 mL) in a 100-mL round-bottom flask and allowed to react, with stirring, for 3 hr while the temperature was maintained at reflux. The resulting mixture was concentrated under vacuum and purified via silica gel column (ethyl acetate:petroleum ether (1:20)) giving 9.5 g (90%) of 5-bromobenzo[d][1,3]dioxole as yellow oil.

Workup

  1. customto react
  2. temperaturewas maintained
  3. temperatureat reflux
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. custompurified via silica gel column (ethyl acetate:petroleum ether (1:20))

Sources & evidence

ORD record
ord-d8dba063cecf455192da47cc3271a6ba
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

Loading…