Tetrabutylammonium Fluoride Trihydrate → 2-tert-Butyl-3-bromo-4-iodopyridine

HRID 921028Notes

Reaction equation

HRID 921028 reaction equation
[C:1]([C:5]1[C:10]([Br:11])=[C:9]([I:12])[CH:8]=[C:7]([Si](C)(C)C)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([C:5]1[C:10]([Br:11])=[C:9]([I:12])[CH:8]=[CH:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 679956892-Tert-butyl-3-bromo-4-iodo-6-trimethylsilylpyridine

Product 1

HCID 679953862-tert-Butyl-3-bromo-4-iodopyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 14.8 g (36 mmol) of 2-tert-butyl-3-bromo-4-iodo-6-trimethylsilylpyridine and 14.0 g (40 mmol) of tetrabutylammonium fluoride trihydrate in 150 ml of THF is heated under reflux for 5 min. After cooling and removal of the THF in vacuo, the residue is taken up in 200 ml of dichloromethane, the org. phase is washed five times with 100 ml of water each time and dried over sodium sulfate. After removal of the dichloromethane in vacuo, the residue is recrystallised from ethanol. Yield: 9.2 g (27 mmol), 75%. Purity: >95% according to 1H-NMR.

Workup

  1. temperatureunder reflux for 5 min
  2. temperatureAfter cooling
  3. customremoval of the THF in vacuo
  4. washphase is washed five times with 100 ml of water each time
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of the dichloromethane in vacuo
  7. customthe residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-6a0d4bae482a48cabc4b03e1b291913c
Source dataset
uspto-grants-2016_03
Patent number
US09273080B2

Reaction notes

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