N-bromobutanimide → 2,3-Dibromo-6-methoxypyridine

HRID 2357930Notes

Reaction equation

HRID 2357930 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[N:11]=1>C(#N)C>[Br:9][C:10]1[C:15]([Br:8])=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[N:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2568102-Bromo-6-methoxypyridine

Product 1

HCID 593893172,3-Dibromo-6-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

NBS (302 g) was added to the compound of Example 259 (295 g) in acetonitrile (575 mL) and the mixture was stirred at 80 to 90° C. for 1 day in a nitrogen atmosphere. After cooling, the crystallized imide was removed by filtration and the filtrate was concentrated. Purification of the resulting residue by silica gel column chromatography (ether:petroleum ether=1:1) gave a 6:1 mixture of the title compound and 2,5-dibromo form. This product was crystallized from cold petroleum ether to afford the title compound as a colorless powder (223 g).

Workup

  1. temperatureAfter cooling
  2. customthe crystallized imide was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customPurification of the resulting residue by silica gel column chromatography (ether:petroleum ether=1:1)
  5. customgave

Sources & evidence

ORD record
ord-93ee9fdcf12b4cd785e0e92176f5cd17
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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