Iodine chloride → 2,2,2-trichloro-1-(4-iodo-1H-pyrrol-2-yl)ethan-1-one

HRID 2090396Notes

Reaction equation

HRID 2090396 reaction equation
[Cl:1][C:2]([Cl:11])([Cl:10])[C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[I:12]Cl>C(Cl)Cl>[Cl:11][C:2]([Cl:1])([Cl:10])[C:3]([C:5]1[NH:6][CH:7]=[C:8]([I:12])[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 3214872-(Trichloroacetyl)pyrrole

Product 1

HCID 116816022,2,2-trichloro-1-(4-iodo-1H-pyrrol-2-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

At r.t. to a solution of 2,2,2-trichloro-1-(1H-pyrrol-2-yl)ethanone (10.0 g, 47.1 mmol) in methylene chloride (80 mL) was added dropwise a solution of iodine monochloride (8.406 g, 51.77 mmol) in methylene chloride (40 mL) with stirring. After completion of addition the mixture was stirred at r.t. for additional 2 h. The mixture was diluted with methylene chloride, quenched with saturated Na2S2O3 solution. After separation the organic solution was washed with water and brine, dried over Na2SO4, filtered, and concentrated to give the crude product which was directly used in the next reaction without further purification.

Workup

  1. additionAfter completion of addition the mixture
  2. stirringwas stirred at r.t. for additional 2 h
  3. customquenched with saturated Na2S2O3 solution
  4. customAfter separation the organic solution
  5. washwas washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1a951c73183d44cab5a372593820ea43
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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