Dibromomethane → 4-Bromo-1,3-benzodioxole

HRID 1251364Notes

Reaction equation

HRID 1251364 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[Br:9].[F-].[K+].[CH2:12](Br)Br>CN(C=O)C>[CH2:12]1[O:8][C:7]2[C:2](=[C:3]([Br:9])[CH:4]=[CH:5][CH:6]=2)[O:1]1

Participants

5

Reactant 3

HCID 3024DibromomethaneHCID 266591,2-Benzenediol, 3-bromo-HCID 522689Potassium Fluoride

Product 1

HCID 27761894-Bromo-1,3-benzodioxoleYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

To 2,3-dihydroxy-bromobenzene (3.0 g, 0.16 mole), KF (4.63 g, 0.080 mole), DMF (15 mL was added CH2Br2 (4.13 g, 0.024 moles). This suspension was heated to 135° C. for 3 hours, cooled and filtered. The filtrate was poured into 200 mL of ether and washed with water, 1 N KOH and brine. The organic layer was dried over magnesium sulfate, filtered and the solvent removed under vacuum, to yield 2,3-Methylenedioxy-bromobenzene (1.45 g, 45 % yield).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. additionThe filtrate was poured into 200 mL of ether
  4. washwashed with water, 1 N KOH and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-966e1995263f40bcb81f4af0d7c3253a
Source dataset
uspto-grants-2002_01
Patent number
US06342504B1

Reaction notes

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