2,6-Dibromopyridine → 2-Bromo-6-tert-butylpyridine

HRID 564821Notes

Reaction equation

HRID 564821 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[CH3:9][C:10]([CH3:13])([O-])[CH3:11].[K+]>C(O)(C)(C)C>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:10]([CH3:13])([CH3:11])[CH3:9])[N:3]=1

Participants

4

Reactant 2

HCID 122742,6-DibromopyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 221134152-Bromo-6-tert-butylpyridineYield 47.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

2,6-Dibromopyridine (50 g) was added to a solution of potassium tert-butoxide (35.5 g) in tert-butanol (300 ml). The mixture was heated to reflux for 3.5 hours then cooled and concentrated. The residue was quenched with water and extracted into ethyl acetate. The combined organic extracts were washed with brine, dried and concentrated to give 2-bromo-6-tert-butylpyridine (21.4 g, 44% yield ) as a clear oil; 1H NMR (270 MHz): δ 1.55(9H,s), 6.58(1H,d), 6.98(1H,d), 7.33(1H,t)ppm.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3.5 hours
  3. temperaturethen cooled
  4. concentrationconcentrated
  5. customThe residue was quenched with water
  6. extractionextracted into ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-41301ede9fe64899b2e969e7f8f2bd65
Source dataset
uspto-grants-2001_01
Patent number
US06169101A

Reaction notes

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