Bromine → Methyl 4-bromo-7-methoxy-2H-1,3-benzodioxole-5-carboxylate

HRID 258153Notes

Reaction equation

HRID 258153 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[O:15][CH2:14][O:13][C:5]=2[CH:6]=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9].[Br:16]Br>C(O)(=O)C>[Br:16][C:6]1[C:5]2[O:13][CH2:14][O:15][C:4]=2[C:3]([O:2][CH3:1])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 24408BromineHCID 601780Methyl 3,4-methylenedioxy-5-methoxybenzoate

Product 1

HCID 11449108Methyl 4-bromo-7-methoxy-2H-1,3-benzodioxole-5-carboxylateYield 51%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 35 ml of acetic acid was dissolved 10.5 g of methyl 5-methoxy-3,4-methylenedioxybenzoate, and a solution of bromine (formed by diluting 8 g of bromine with 25 ml of acetic acid) was dropped into the solution over a period of 1 hour. The mixture was stirred at room temperature for 10 hours and the reaction liquid was poured into ice water, and the formed precipitate was recovered by filtration and recrystallized from ethanol to obtain methyl 2-bromo-5-methoxy-3,4-methylenedioxybenzoate (the yield was 51%).

Workup

  1. customthe reaction liquid
  2. filtrationthe formed precipitate was recovered by filtration
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-721af72956c94556ae745bc4f58863fa
Source dataset
uspto-grants-1993_11
Patent number
US05264594

Reaction notes

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