Bromine → HCID 10742622, compound

HRID 256597Notes

Reaction equation

HRID 256597 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([N:13]2[CH:17]=[CH:16][CH:15]=[C:14]2[C:18](=[O:23])[C:19]([Cl:22])([Cl:21])[Cl:20])[CH2:11][C:10](=[O:12])[NH:9][C:7]1=[O:8])=[O:5])[CH3:2].[Br:24]Br.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Br:24][C:16]1[CH:15]=[C:14]([C:18](=[O:23])[C:19]([Cl:22])([Cl:20])[Cl:21])[N:13]([C:6]2([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][C:10](=[O:12])[NH:9][C:7]2=[O:8])[CH:17]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 10667564HCID 10667564, compound

Product 1

HCID 10742622HCID 10742622, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 2-ethoxycarbonyl-2-(2-trichloroacetylpyrrol-1-yl)succinimide (6.0 g) in chloroform (30 ml) was added dropwise a solution of bromine (6.9 g) in chloroform (18 ml) under ice cooling. The resulting mixture was stirred under ice cooling for 30 minutes, poured into aqueous sodium bicarbonate solution, and extracted with chloroform. The extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on silica gel using chloroform/methanol (2000:1) as the eluent. Fractions containing the title compound were pooled and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (2.4 g, 36.4%) as colorless crystals, mp 196°-198° C.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extracts were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed on silica gel
  5. additionFractions containing the title compound
  6. customevaporated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-d7dc5668f2f74e91ad298176615db973
Source dataset
uspto-grants-1993_11
Patent number
US05258382

Reaction notes

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