Hydrogen Bromide → 4-Bromo-3-nitropyridine

HRID 2423617Notes

Reaction equation

HRID 2423617 reaction equation
CO[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10].[BrH:12]>C1(C)C=CC=CC=1>[Br:12][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 3558324-Methoxy-3-nitropyridine

Product 1

HCID 27629204-Bromo-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To 4-methoxy-3-nitropyridine (3.5 g) was added 48% hydrobromic acid (30 ml), and the solution was stirred overnight at 80° C. Toluene was added thereto followed by stirring. The solvent was evaporated in vacuo. To the total amount of the resulting 3-nitropyridin-4-ol (crude product) were added phosphorous oxybromide (20 g) and chloroform (30 ml), and the solution was stirred for 2 hours at 110° C. To the reaction mixture was added an ice, the solution was neutralized with aqueous ammonia, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, then filtered through silica gel, and the solvent was evaporated in vacuo to provide the title compound (2.6 g).

Workup

  1. stirringby stirring
  2. customThe solvent was evaporated in vacuo
  3. additionTo the total amount of the resulting 3-nitropyridin-4-ol (crude product) were added phosphorous oxybromide (20 g) and chloroform (30 ml)
  4. stirringthe solution was stirred for 2 hours at 110° C
  5. additionTo the reaction mixture was added an ice
  6. extractionextracted with ethyl acetate
  7. washsequentially washed with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered through silica gel
  10. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-36d43b701868457d87acc8d389059d5b
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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