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

HRID 1978616Notes

Reaction equation

HRID 1978616 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.C(=O)([O-])[O-].[Na+].[Na+].[Br:17]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>CCCCCC>[Br:17][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

6

Reactant 4

HCID 103011,4-BenzodioxanHCID 10340Sodium CarbonateHCID 24408BromineHCID 24477Sodium Thiosulfate

Product 1

HCID 1041416-Bromo-1,4-benzodioxane

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

To a mixture of 1,4-benzodioxane (5.0 g) and sodium carbonate (5.9 g) in hexane (100 ml) was added dropwise at room temperature a solution of bromine (1.9 ml) in hexane (20 ml) for 1 hour and the mixture was stirred for 1 hour. To the mixture was added an aqueous solution of sodium thiosulfate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give orange oil of 6-bromo-2,3-dihydro-1,4-benzodioxine (7.48 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92086d4d1603413ab9a0fc3fd7f1cf58
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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