N-bromobutanimide → 2-Bromomethyl-3-methoxy-4-propoxypyridine

HRID 649212Notes

Reaction equation

HRID 649212 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:13])=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH3:12].[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:4]1[C:3]([O:2][CH3:1])=[C:8]([O:9][CH2:10][CH2:11][CH3:12])[CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 139829483-Methoxy-2-methyl-4-propoxypyridine

Product 1

HCID 139829492-Bromomethyl-3-methoxy-4-propoxypyridineYield 27.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 3-methoxy-2-methyl-4-propoxypyridine (1.0 g) in carbon tetrachloride (70 ml), was added N-bromosuccinimide (1.0 g) and the mixture was irradiated with and infrared lamp (Toshiba, 100 V, 375 WR) for 2 hours at reflux. An insoluble substance was filtered off, and the filtrate was concentrated and purified by column chromatography on silica gel, to give 2-bromomethyl-3-methoxy-4-propoxypyridine (0.4 g) as a reddish brown oil.

Workup

  1. customthe mixture was irradiated with and infrared lamp (Toshiba, 100 V, 375 WR) for 2 hours
  2. temperatureat reflux
  3. filtrationAn insoluble substance was filtered off
  4. concentrationthe filtrate was concentrated
  5. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9f78191aeaa34476b9bab799e707e6f2
Source dataset
uspto-grants-1988_04
Patent number
US04738975

Reaction notes

Loading…