Acetic Anhydride → (4-Bromopyridin-2-yl)methyl acetate

HRID 605957

Reaction equation

HRID 605957 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N+:5]([O-])=[C:4]([CH3:9])[CH:3]=1.[C:10]([O:13]C(=O)C)(=[O:12])[CH3:11]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:9][O:13][C:10](=[O:12])[CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 544461394-Bromo-2-methyl-1-oxo-1lambda~5~-pyridine

Product 1

HCID 45789873(4-Bromopyridin-2-yl)methyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-methylpyridine-1-oxide (4.00 g, 21.40 mmol) in DCM (20 mL) is added acetic anhydride (6 mL). The mixture is stirred at room temperature for 1 hour and then heated at reflux overnight. The solvent is removed under vacuum and the crude product is filtered through a silica plug, eluting with DCM to afford the title compound as an orange oil (815 mg).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe solvent is removed under vacuum
  4. filtrationthe crude product is filtered through a silica plug
  5. washeluting with DCM

Sources & evidence

ORD record
ord-38636f2731b94ebe82902bd00ee169fc
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Linked notes

Loading…