1,4-Benzodioxan → 6-Bromo-1,4-benzodioxane

HRID 1814729Notes

Reaction equation

HRID 1814729 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[Br:11]N1C(=O)CCC1=O>CN(C)C=O>[Br:11][C:9]1[CH:8]=[CH:7][C:6]2[O:1][CH2:2][CH2:3][O:4][C:5]=2[CH:10]=1

Participants

4

Reactant 2

HCID 103011,4-BenzodioxanHCID 67184N-bromobutanimide

Product 1

HCID 1041416-Bromo-1,4-benzodioxane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

35 g of 1,4-benzodioxane and 200 ml of anhydrous dimethylformamide are placed under argon at 0° C. 54.9 g of N-bromosuccinimide are then added in portions. After it has returned gradually to room temperature, the reaction mixture is stirred for 24 hours. The solvents are evaporated off under reduced pressure and the white solid obtained is washed with dichloromethane. The filtrate is treated with 50 ml of saturated aqueous sodium sulfate solution, washed with 50 ml of saturated aqueous sodium chloride solution and dried over magnesium sulfate. After evaporation of the solvents under reduced pressure, a yellow oil is obtained (quantitative yield).

Workup

  1. customare placed under argon at 0° C
  2. customhas returned gradually to room temperature
  3. customThe solvents are evaporated off under reduced pressure
  4. customthe white solid obtained
  5. washis washed with dichloromethane
  6. additionThe filtrate is treated with 50 ml of saturated aqueous sodium sulfate solution
  7. washwashed with 50 ml of saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. customAfter evaporation of the solvents under reduced pressure
  10. customa yellow oil is obtained (quantitative yield)

Sources & evidence

ORD record
ord-5a63ab5bb6204fe0aacb73c0310cd7a0
Source dataset
uspto-grants-2005_04
Patent number
US06878665B2

Reaction notes

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