2,6-Dichloro-4-iodopyridine → 2-Tert-butoxy-6-chloro-4-iodopyridine

HRID 68337Notes

Reaction equation

HRID 68337 reaction equation
Cl[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH3:10][C:11]([CH3:14])([O-:13])[CH3:12].[K+]>O1CCCC1.C(OCC)(=O)C>[C:11]([O:13][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([Cl:9])[N:3]=1)([CH3:14])([CH3:12])[CH3:10]

Participants

5

Reactant 2

HCID 117373932,6-Dichloro-4-iodopyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 584762982-Tert-butoxy-6-chloro-4-iodopyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,6 dichloro-4-iodo pyridine (1 g, 3.65 mmol) in 15 mL tetrahydrofuran was added 1M potassium tert-butoxide (4.02 mL, 4.02 mmol) and the solution heated at reflux for 2 hours. The mixture was diluted with ethyl acetate, washed with water and brine and dried over magnesium sulfate, filtered and concentrated. The crude material was used without further purification. MS (DCI) m/e 312.0 (M+H)+.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 2 hours
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was used without further purification

Sources & evidence

ORD record
ord-752080f4e40a49149c26a0ab1aa4e35c
Source dataset
uspto-grants-2014_09
Patent number
US08822446B2

Reaction notes

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