Sodium Iodide → 5-Iodo-2-(trifluoromethyl)benzonitrile

HRID 573781Notes

Reaction equation

HRID 573781 reaction equation
[I-:1].[Na+].Br[C:4]1[CH:5]=[CH:6][C:7]([C:12]([F:15])([F:14])[F:13])=[C:8]([CH:11]=1)[C:9]#[N:10]>O1CCOCC1.[Cu]I>[I:1][C:4]1[CH:5]=[CH:6][C:7]([C:12]([F:15])([F:14])[F:13])=[C:8]([CH:11]=1)[C:9]#[N:10]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 509981335-Bromo-2-(trifluoromethyl)benzonitrile

Product 1

HCID 667621505-Iodo-2-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

In a microwave vial 2.24 g 5-bromo-2-(trifluoromethyl)benzonitrile are dissolved in 10 ml 1,4-dioxane. 90 mg copper-(I)-iodide and 2.7 g sodium iodide are added and the mixture is purged for 5 minutes with argon. 142 μl trans-N,N′-dimethylcyclohexane-1,2-diamine and 1.9 ml hexamethyldisilazane are added and the mixture is heated for 6 hours to 110° C. The mixture is diluted in 100 ml 4 M hydrochloric acid and stirred for 10 minutes. This aqueous phase is three times extracted with dichloromethane. The combined organic phases are washed with brine and dried with magnesium sulphate. The solvents are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethylacetate 85:15).

Workup

  1. customthe mixture is purged for 5 minutes with argon
  2. addition142 μl trans-N,N′-dimethylcyclohexane-1,2-diamine and 1.9 ml hexamethyldisilazane are added
  3. temperaturethe mixture is heated for 6 hours to 110° C
  4. additionThe mixture is diluted in 100 ml 4 M hydrochloric acid
  5. extractionextracted with dichloromethane
  6. washThe combined organic phases are washed with brine
  7. dry with materialdried with magnesium sulphate
  8. customThe solvents are evaporated in vacuo
  9. customthe residue is chromatographed on silica gel (cyclohexane/ethylacetate 85:15)

Sources & evidence

ORD record
ord-137e44afbc394a7dbf9663a16e51ff8b
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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