Iodine → HCID 178516139, compound

HRID 1519805Notes

Reaction equation

HRID 1519805 reaction equation
[I:1]I.[F:3][C:4]([F:13])([F:12])[C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][N:6]=1.C([O-])([O-])=O.[K+].[K+]>CO>[I:1][C:8]1[C:9]([OH:11])=[CH:10][C:5]([C:4]([F:3])([F:12])[F:13])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 11430Potassium CarbonateHCID 178516505HCID 178516505, compound

Product 1

HCID 178516139HCID 178516139, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Iodine (8.16 g, 32.1 mmol) was added in five portions to a solution of 2-(trifluoromethyl)pyridin-4-ol (5 g, 30.65 mmol) and K2CO3 (4.66 g, 33.7 mmol) in methanol (34 mL) at 0° C. and the resulting mixture was stirred at room temperature for 20 h. The solution was washed with saturated aqueous sodium sulfite then acetic acid (10 mL) was added and the solution was extracted with ethyl acetate, dried (Na2SO4), filtered, concentrated under vacuum and the residue was purified on a silica gel column to give 5-iodo-2-(trifluoromethyl)pyridin-4-ol (5.1 g, 57%). Retention time (min)=1.761, method [1], MS(ESI) 290.9 (M+H).

Workup

  1. washThe solution was washed with saturated aqueous sodium sulfite
  2. additionacetic acid (10 mL) was added
  3. extractionthe solution was extracted with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-77673349fd2d40c9951f6e8d3bb76727
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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