Water → 4-Bromo-7-methoxybenzo[d][1,3]dioxole

HRID 2084823Notes

Reaction equation

HRID 2084823 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]Br.[F-].[K+].O>CN(C=O)C>[Br:1][C:2]1[C:3]2[O:11][CH2:13][O:5][C:4]=2[C:6]([O:9][CH3:10])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3024DibromomethaneHCID 522689Potassium FluorideHCID 37058743-Bromo-6-methoxybenzene-1,2-diol

Product 1

HCID 111389764-Bromo-7-methoxybenzo[d][1,3]dioxole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

3-Bromo-6-methoxycatechol (23.4 g) was dissolved in DMF (150 ml), and dibromomethane (15.4 ml) and potassium fluoride (31.1 g) were added thereto, followed by heating at 110° C. for 6 hours with stirring. After being allowed to stand for cooling, water was added to the mixture followed by extraction with ether. The organic layer was washed with an aqueous solution of sodium hydroxide, with water, and with a saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/1) to give Compound IIbj-a (5.6 g, 40%) as a white solid.

Workup

  1. temperaturefor cooling
  2. extractionfollowed by extraction with ether
  3. washThe organic layer was washed with an aqueous solution of sodium hydroxide, with water
  4. dry with materialwith a saturated saline, and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/1)
  7. customto give Compound IIbj-a (5.6 g, 40%) as a white solid

Sources & evidence

ORD record
ord-fbcadfa74f2441ca898eee61cc79b028
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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