Phosphorus oxychloride → 5-Bromo-2-chloro-3-nitropyridine

HRID 1628320Notes

Reaction equation

HRID 1628320 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.P(Cl)(Cl)([Cl:14])=O>>[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

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178418997HCID 178418997, compound

Product 1

HCID 70194125-Bromo-2-chloro-3-nitropyridineYield 45%

Conditions

Temperature
100 °C

Procedure

To 5-bromo-3-nitropyridin-2-ol (78.A)(1 g, 5 mmol) was added 10 mL of phosphorus oxychloride. The reaction was heated at 100° C. for 1 hr., concentrated and worked up between EtOAc and saturated NaHCO3. The organic layer was concentrated, redissolved in DCM, filtered off the solids. The DCM layer was concentrated again to afford 450 mg (45%) of 78.B.

Workup

  1. concentration, concentrated
  2. concentrationThe organic layer was concentrated
  3. dissolutionredissolved in DCM
  4. filtrationfiltered off the solids
  5. concentrationThe DCM layer was concentrated again

Sources & evidence

ORD record
ord-c7cd7acc23a540cda0ed1c35c2a61d62
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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