Iodine → Ethyl 4-bromo-1,2-dimethyl-5-(p-toluoyl)pyrrole-3-carboxylate

HRID 2071689Notes

Reaction equation

HRID 2071689 reaction equation
[Br:1]Br.[CH3:3][N:4]1[C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[O:10])=[CH:7][C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:5]1[CH3:23].II>C(Cl)(Cl)Cl>[Br:1][C:7]1[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:5]([CH3:23])[N:4]([CH3:3])[C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 807IodineHCID 24408BromineHCID 21411872Ethyl 1,2-dimethyl-5-(p-toluoyl)pyrrole-3-carboxylate

Product 1

HCID 21411860Ethyl 4-bromo-1,2-dimethyl-5-(p-toluoyl)pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 27.4 ml (0.538 mole) of bromine in 150 ml of chloroform is added to a refluxing solution of 152.6 g. (0.538 mole) of ethyl 1,2-dimethyl-5-(p-toluoyl)pyrrole-3-carboxylate in 1500 ml of chloroform containing a few iodine crystals over a period of 45 min. The solution is heated under reflux for 10 min. and is then poured into ice water. The organic layer is separated and washed with sodium bicarbonate solution, sodium bisulfate solution, and brine. It is then dried over sodium sulfate and the solvent is evaporated in vacuo. After recrystallization of the product from methanol, it is extracted in a Soxhlet extractor with about one liter of diethyl ether and then crystallized from the cooled ether to yield ethyl 4-bromo-1,2-dimethyl-5-(p-toluoyl)pyrrole-3-carboxylate; m.p. 122°-125° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureunder reflux for 10 min.
  3. customThe organic layer is separated
  4. washwashed with sodium bicarbonate solution, sodium bisulfate solution, and brine
  5. dry with materialIt is then dried over sodium sulfate
  6. customthe solvent is evaporated in vacuo
  7. customAfter recrystallization of the product from methanol, it
  8. extractionis extracted in a Soxhlet extractor with about one liter of diethyl ether
  9. customcrystallized from the cooled ether

Sources & evidence

ORD record
ord-dc38d72a02074cd88807de1383eb58e1
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

Loading…