Water → 5-Bromo-8-methoxy-2,3-dihydrobenzo[B][1,4]dioxine

HRID 1057944

Reaction equation

HRID 1057944 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:4]([OH:5])[C:3]=1[OH:11].Br[CH2:13][CH2:14]Br.[F-].[K+].O>CN(C=O)C>[Br:1][C:2]1[C:3]2[O:11][CH2:14][CH2:13][O:5][C:4]=2[C:6]([O:9][CH3:10])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 522689Potassium FluorideHCID 37058743-Bromo-6-methoxybenzene-1,2-diol

Product 1

HCID 28250155-Bromo-8-methoxy-2,3-dihydrobenzo[B][1,4]dioxine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-bromo-6-methoxycatechol (16 g) was dissolved in DMF (50 ml), mixed with 1,2-dibromoethane (15 ml) and potassium fluoride (21 g), stirred for 6 hours while heating at 110EC. The resultant was allowed to stand for cooling, mixed with water, and extracted with ether. The organic layer was washed withan aqueous sodium hydroxide solution, water, and a saturated aqueous sodium chloride solution in that order, dried over manganese sulfate anhydride, and then, evaporated under reduced pressure for removing the solvent. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give Compound IIbo-a (5.9 g, 34%) as a white solid.

Workup

  1. temperaturewhile heating at 110EC
  2. temperaturefor cooling
  3. extractionextracted with ether
  4. washThe organic layer was washed withan aqueous sodium hydroxide solution, water
  5. dry with materiala saturated aqueous sodium chloride solution in that order, dried over manganese sulfate anhydride
  6. customevaporated under reduced pressure
  7. customfor removing the solvent
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)
  9. customto give Compound IIbo-a (5.9 g, 34%) as a white solid

Sources & evidence

ORD record
ord-6e4b48aa994847d780c89c5b74975537
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Linked notes

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