Sodium Thiosulfate → 3-Bromo-5-chloro-2-methoxy-4-methylpyridine

HRID 242421Notes

Reaction equation

HRID 242421 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:11]([CH3:18])=[CH:12][C:13]([O:16][CH3:17])=[N:14][CH:15]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[Br:1][C:12]1[C:13]([O:16][CH3:17])=[N:14][CH:15]=[C:10]([Cl:9])[C:11]=1[CH3:18]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 231336465-Chloro-2-methoxy-4-methylpyridine

Product 1

HCID 231336453-Bromo-5-chloro-2-methoxy-4-methylpyridineYield 97.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

20.2 g (114 mmol) of N-bromosuccinimide was charged to a N,N-dimethylformamide (DMF) 15 ml solution of 7.2 g (46 mmol) of 5-chloro-2-methoxy-4-methylpyridine, followed by stirring at 50° C. for 20 hours. A diluted sodium thiosulfate aqueous solution was added to the reaction solution, and the aqueous layer was extracted with diethyl ether. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and subjected to filtration on the pad of a silica gel cake, and the solvent was distilled off under reduced pressure to obtain 10.6 g (yield: 97%) of 3-bromo-5-chloro-2-methoxy-4-methylpyridine (melting point: 44 to 45° C.).

Workup

  1. extractionthe aqueous layer was extracted with diethyl ether
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationsubjected to filtration on the pad of a silica gel cake
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8ad5921db5894f448d59391ae3c2d45b
Source dataset
uspto-grants-2014_02
Patent number
US08653113B2

Reaction notes

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