Bromine → HCID 21411820, compound

HRID 2071684Notes

Reaction equation

HRID 2071684 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[Br:27]Br>C(Cl)(Cl)Cl.II>[Br:27][C:9]1[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]([CH3:13])[C:8]=1[C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 21411840HCID 21411840, compound

Product 1

HCID 21411820HCID 21411820, compound

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 20 g. (0.053 mole) of ethyl 5-p-chlorobenzoyl-3-ethoxycarbonyl-1-methylpyrrole- 2-acetate in 200 ml of chloroform containing a few crystals of iodine as catalyst is heated to reflux and a solution of 3.0 ml (0.058 mole) of bromine in 20 ml of CH Cl3 is added over 45 min. The whole is heated under reflux for 11/2 hours, cooled, and washed successively with aqueous sodium bicarbonate solution, aqueous sodium bisulfite solution and brine. After the solution is dried over magnesium sulfate, the solvent is evaporated in vacuo and the resulting residue is recrystallized successively from methycyclohexane and 75% ethanol-water to give ethyl 4-bromo-5-(p-chlorobenzoyl)-3- ethoxycarbonyl-1-methylpyrrole-2-acetate as white crystals; m.p. 88°-90° C.

Workup

  1. temperatureto reflux
  2. temperatureThe whole is heated
  3. temperatureunder reflux for 11/2 hours
  4. temperaturecooled
  5. washwashed successively with aqueous sodium bicarbonate solution, aqueous sodium bisulfite solution and brine
  6. dry with materialAfter the solution is dried over magnesium sulfate
  7. customthe solvent is evaporated in vacuo
  8. customthe resulting residue is recrystallized successively from methycyclohexane and 75% ethanol-water

Sources & evidence

ORD record
ord-8273b14563a847efaa92f9e18f8782c5
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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