Methanol → HCID 86690466, compound

HRID 1026739Notes

Reaction equation

HRID 1026739 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N+:3]=1[O-].CO.[C:13]([O:16]C(=O)C)(=[O:15])[CH3:14]>>[C:13]([O:16][CH2:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Br:1])[N:3]=1)(=[O:15])[CH3:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 86690465HCID 86690465, compound

Product 1

HCID 86690466HCID 86690466, compound

Conditions

Temperature
120 °C

Procedure

A solution of 2-bromo-3-fluoro-6-methylpyridine 1-oxide (585 mg) in acetic anhydride (4.98 mL) was stirred while heating at 120° C. for 4 hr. After returning the solution to room temperature, methanol (25 mL) was gradually added dropwise thereto. After the solvent was distilled off under reduced pressure, the acetic anhydride was evaporated with methanol. The resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=88:12-0:100) to afford (6-bromo-5-fluoropyridin-2-yl)methyl acetate (269 mg).

Workup

  1. customto room temperature
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. customthe acetic anhydride was evaporated with methanol
  4. customThe resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=88:12-0:100)

Sources & evidence

ORD record
ord-78ad9899113345c898ffeff7789e73bd
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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