Phosphorus oxybromide → 2,3-Dibromo-5-nitropyridine

HRID 41994

Reaction equation

HRID 41994 reaction equation
[Br:1][C:2]1[C:3](O)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.P(Br)(Br)([Br:14])=O.P(Br)(Br)Br>O>[Br:14][C:3]1[C:2]([Br:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 24614Phosphorus tribromideHCID 178526832HCID 178526832, compound

Product 1

HCID 12014252,3-Dibromo-5-nitropyridineYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-bromo-5-nitropyridin-2-ol, POBr3 and PBr3 was heated at 120° C. for 3.5 h. The crude mixture was poured into a mixture of ice and water and extracted with DCM. The crude mixture was purified by flash chromatography over SiO2 eluting with hexane/ethyl acetate mixtures affording 2.63 g (yield 73%) of the expected product.

Workup

  1. extractionextracted with DCM
  2. customThe crude mixture was purified by flash chromatography over SiO2 eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-a4e2c39a7efe46fa98d2f35b3345c17e
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Linked notes

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