Tolmetin → [3-Bromo-1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid

HRID 2071673Notes

Reaction equation

HRID 2071673 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=[C:3]1[CH2:16][C:17]([OH:19])=[O:18].[Br:20]Br>C(O)(=O)C>[Br:20][C:4]1[CH:5]=[C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[O:8])[N:2]([CH3:1])[C:3]=1[CH2:16][C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 5509TolmetinHCID 24408Bromine

Product 1

HCID 21411942[3-Bromo-1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of 2.0g. (0.0078 moles) of 1-methyl- 5-(p-toluoyl)pyrrole-2-acetic acid in 40 ml. of glacial acetic acid is added dropwise a solution of 1.2g (0.0078 moles) of bromine in 3 ml. of glacial acetic acid. The mixture is stirred at room temperature for two hours, after which it is poured into 300 ml. of water, and the solid which forms is filtered off. Recrystallization from ether-hexane yields 3-bromo-1-methyl-5-(p-toluoyl) pyrrole-2-acetic acid as a white solid; m.p. 162°-164° C.

Workup

  1. additionafter which it is poured into 300 ml
  2. filtrationof water, and the solid which forms is filtered off
  3. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-ef0d343bdc214a20bd2744d906dd9bdb
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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