Iodine → HCID 639443, compound

HRID 342879Notes

Reaction equation

HRID 342879 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.II.[F:15]F>S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>[F:15][C:4]1[CH:3]=[C:2]([Cl:1])[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 807IodineHCID 68664,7-DichloroquinolineHCID 24524Fluorine2×

Product 1

HCID 639443HCID 639443, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 656671Sodium PyrosulfiteSolvent

Procedure

A solution containing 4,7-dichloroquinoline (1.0 g, 5 mmol) and iodine (1.28 g, 5 mmol) in CF2ClCFCl2 (30 ml) was placed in a fluorination apparatus fitted with a drying tube filled with soda lime. Elemental fluorine (7 mmol) as a 10% mixture by volume in dry nitrogen was then passed through the stirred solution using narrow bore PTFE tubing at ca. 15 ml/min. After the fluorine had been added, the solution was poured into 10% aqueous sodium metabisulfite solution (30 ml) and extracted with dichloromethane. The organic extracts were dried and evaporated to an oil (0.98 g). GC/MS analysis showed a 34% conversion of starting material. Column chromatography on silica gel with dichloromethane as eluant gave 2-fluoro-4,7-dichloroquinoline (0.33 g, 87%) as white crystals; other data were the same as that described in the following reaction.

Workup

  1. customfitted with a drying tube
  2. extractionextracted with dichloromethane
  3. customThe organic extracts were dried
  4. customevaporated to an oil (0.98 g)

Sources & evidence

ORD record
ord-43c160db012e465fa3c34fcf418b07d1
Source dataset
uspto-grants-1999_01
Patent number
US05859255

Reaction notes

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