N-bromobutanimide → 2-Bromo-3,5-dimethoxypyridine

HRID 1258430Notes

Reaction equation

HRID 1258430 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Br:11]N1C(=O)CCC1=O>CC#N>[Br:11][C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([O:9][CH3:10])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 8177333,5-Dimethoxypyridine

Product 1

HCID 543319912-Bromo-3,5-dimethoxypyridineYield 70.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3,5-dimethoxypyridine (780 mg, 5.6 mmol) in dry MeCN (24 ml) was added N-bromosuccinimide (1.0 g, 5.6 mmol) and the reaction was heated to reflux for 1 hour. After cooling, the solvent was removed under vacuum and the residue was triturated with diethyl ether to precipitate the succinimide by-product and filtered. The filtrate was concentrated onto silica-gel and the residue purified by flash chromatography (silica-gel, eluted with hexanes:EtOAc, 3:1) to afford the product as a white solid (860 mg, 70%). 1H-NMR (300 MHz, CDCl3) δ 7.67 (d, J=2.5 Hz, 1H), 6.71 (d, J=2.5 Hz, 1H), 3.87 (s, 3H), 3.85 (s, 3H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. customthe solvent was removed under vacuum
  5. customthe residue was triturated with diethyl ether
  6. customto precipitate the succinimide by-product
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated onto silica-gel
  9. customthe residue purified by flash chromatography (silica-gel, eluted with hexanes:EtOAc, 3:1)

Sources & evidence

ORD record
ord-6bb3636e358f41979b9e78611b16a17f
Source dataset
uspto-grants-2013_06
Patent number
US08466163B2

Reaction notes

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