Ethanol → 2-Bromo-6-ethoxypyridine

HRID 2104990Notes

Reaction equation

HRID 2104990 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Na].C(O)C.Br[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[N:11]=1>CCOC(C)=O>[Br:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([O:1][CH2:2][CH3:3])[N:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 122742,6-DibromopyridineHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 12010182-Bromo-6-ethoxypyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a sodium ethoxide solution, prepared by addition of sodium (36 mg, 1.58 mmol) to ethanol (2 mL), was added 2,6-dibromopyridine (250 mg, 1.06 mmol). The mixture was stirred at 90° C. for 2.5 h, then was diluted with EtOAc. The organic phase was washed with water (2×) and brine, dried (Na2SO4) and concentrated. The crude material was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient) to afford 163 mg of 156.1 as a colorless oil. LCMS (2 min gradient) RT=1.68 min, 202.1 (M+H)+.

Workup

  1. washThe organic phase was washed with water (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude material was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-91d6026033e94c75baf8af8740d5246e
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

Loading…