Water → 3-Bromo-2-methoxypyridine

HRID 1049463Notes

Reaction equation

HRID 1049463 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:9][OH:10].C[O-].[Na+].O>CN(C=O)C>[Br:1][C:2]1[C:3]([O:10][CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Conditions

Temperature
80 °C

Procedure

Under an argon atmosphere, to a solution of 3-bromo-2-chloropyridine (4.76 g) in DMF (30 mL) was added 28% sodium methoxide methanol solution (5.73 g) at room temperature, and the mixture was stirred at 80° C. for 30 min. Water was added at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound (4.43 g) as a pale-yellow oil. This compound was used for the next step without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c11ec9b5c79540198f0d0cceed6cb226
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

Loading…