Thionyl Chloride → 5-Bromo-2-chloro-3-nitropyridine

HRID 2096965Notes

Reaction equation

HRID 2096965 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](O)=[N:6][CH:7]=1.S(Cl)([Cl:14])=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([Cl:14])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178418997HCID 178418997, compound

Product 1

HCID 70194125-Bromo-2-chloro-3-nitropyridineYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N′-dimethylformamide (3 mL) was added to a mixture of 5-bromo-2-hydroxy-3-nitropyridine (16.54 g, 80 mmol) and thionyl chloride (43 mL) and the mixture was stirred and heated to reflux. After 1 hour, the solution was cooled and the solvent was evaporated. The mixture was co-evaporated with toluene to give a dark solid. Purification by flash chromatography (10:1 hexanes/ethyl acetate) gave the title compound (14.63 g, 82%) as a yellow solid.

Workup

  1. temperatureheated to reflux
  2. temperaturethe solution was cooled
  3. customthe solvent was evaporated
  4. customto give a dark solid
  5. customPurification by flash chromatography (10:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e2b52d5fce2c49c694e6d48a64e9258f
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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