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

HRID 840455Notes

Reaction equation

HRID 840455 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]I>FC(F)(F)C([O-])=O.[Ag+].C(Cl)(Cl)Cl>[I:12][C:8]1[CH:9]=[C:5]([C:3](=[O:4])[C:2]([Cl:1])([Cl:10])[Cl:11])[NH:6][CH:7]=1

Participants

5

Reactant 2

HCID 807IodineHCID 3214872-(Trichloroacetyl)pyrrole

Product 1

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

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6212ChloroformSolvent

Procedure

8.4 g (39.5 mmol) of 2-trichloroacetylpyrrole and 100 ml of chloroform were introduced into a three-necked flask under a stream of nitrogen and 8.6 g (39.5 mmol) of silver trifluoroacetate and 10.16 g (39.5 mmol) of iodine were added successively. Stirring was carried out at room temperature for one hour and the reaction mixture was poured into ice and extracted with dichloromethane. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was triturated in hexane and filtered. 8.2 g (61%) of the expected compound, with a melting point of 118°-119° C., were recovered.

Workup

  1. additionwere added successively
  2. additionthe reaction mixture was poured into ice
  3. extractionextracted with dichloromethane
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue obtained
  8. customwas triturated in hexane
  9. filtrationfiltered
  10. custom8.2 g (61%) of the expected compound, with a melting point of 118°-119° C., were recovered

Sources & evidence

ORD record
ord-155485f339ff479086da15dab5bbdff3
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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