Bromine → 6-bromo-1,3-benzodioxol-5-ol

HRID 2308896Notes

Reaction equation

HRID 2308896 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][CH:5]=[C:6]([OH:10])[CH:7]=2)[O:2]1.[Br:11]Br>C(O)(=O)C>[Br:11][C:5]1[CH:4]=[C:3]2[O:2][CH2:1][O:9][C:8]2=[CH:7][C:6]=1[OH:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 68289Sesamol

Product 1

HCID 2291486-bromo-1,3-benzodioxol-5-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 0.18 mol (25 g) of 4,5-methylenedioxyphenol in 125 ml of glacial acetic acid, a solution of 0.16 mol (29 g) of bromine in 145 ml of glacial acetic acid is added slowly, the temperature of the reaction medium being maintained at between 15° and 25° C. When the addition is complete, the reaction medium is poured into 1.5 liters of ice-cold water. The expected product precipitates. After being drained, it is washed with water until the solvent has been removed. After being dried under vacuum in the presence of potassium hydroxide, it is recrystallized from a petroleum ether/ethyl acetate mixture or from cyclohexane. It melts at 84° C. (decomposition).

Workup

  1. temperaturethe temperature of the reaction medium being maintained at between 15° and 25° C
  2. additionWhen the addition
  3. customThe expected product precipitates
  4. washit is washed with water until the solvent
  5. customhas been removed
  6. dry with materialAfter being dried under vacuum in the presence of potassium hydroxide, it
  7. customis recrystallized from a petroleum ether/ethyl acetate mixture or from cyclohexane

Sources & evidence

ORD record
ord-5dae2254812e49be9a92ad83db6bb0aa
Source dataset
uspto-grants-1987_09
Patent number
US04692166

Reaction notes

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