Iodine → HCID 22645647, compound

HRID 1060791Notes

Reaction equation

HRID 1060791 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[CH:17]=[C:16]([Si](C)(C)C)[N:15]=[N:14]1.[I:22]I>O1CCCC1.FC(F)(F)C([O-])=O.[Ag+]>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[CH:17]=[C:16]([I:22])[N:15]=[N:14]1

Participants

5

Reactant 2

HCID 807IodineHCID 10066685HCID 10066685, compound

Product 1

HCID 22645647HCID 22645647, compound

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trimethylsilyl- 1,2,3-triazole (EP-400842-A1; 1.00 g) in tetrahydrofuran (20 ml) was added silver trifluoroacetate (623 mg) and iodine (716 mg) at −78° C. under an atmosphere of nitrogen. The reaction was allowed to warm to room temperature over 1 hour and then left to stir for a further 16 hours. The reaction was filtered and the filtrate diluted with water (100 ml) and extracted with ether (100 ml), the organic fraction was separarted, dried over MgSO4, filtered and evaporated to dryness. The residue was purified by column chromatography (silica, 100 g) eluted with dichloromethane:hexane (2:1) to give the title compound as a pale yellow crystalline material, m.p. 194-195° C.

Workup

  1. waitleft
  2. filtrationThe reaction was filtered
  3. additionthe filtrate diluted with water (100 ml)
  4. extractionextracted with ether (100 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by column chromatography (silica, 100 g)
  9. washeluted with dichloromethane:hexane (2:1)

Sources & evidence

ORD record
ord-f27ba657eed44d47929850ae6cb08325
Source dataset
uspto-grants-2003_02
Patent number
US06525079B2

Reaction notes

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