Sodium Hydroxide → 2-Bromo-3-methyl-5-nitropyridine

HRID 928640

Reaction equation

HRID 928640 reaction equation
[CH3:1][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:13].[OH-].[Na+]>C1(C)C=CC=CC=1.CN(C=O)C>[Br:13][C:3]1[C:2]([CH3:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 178428770HCID 178428770, compound

Product 1

HCID 52004662-Bromo-3-methyl-5-nitropyridineYield 99%

Reagents, catalysts & solvents 1

HCID 21735183Dimethylformamide tolueneSolvent

Conditions

Temperature
120 °C

Procedure

A sample of 3-methyl-5-nitropyridin-2-ol (1.44 g, 9.34 mmol) was placed in 35 mL pressure vessel and dissolved in a mixture of toluene/DMF (10:1 ratio; 15 mL). The vessel was capped with a septum, flushed with Argon and phosphorous tribromide (1.32 mL, 14.0 mmol) was added by syringe. The septum cap was replaced by a Teflon cap and the mixture was stirred for 20 min at 120° C. The mixture was cooled to room temperature, neutralized with a 3M NaOH solution and extracted with toluene (3×). The combined organic phases were dried over anhydrous MgSO4 and concentrated under vacuum to give 2.00 g of the desired 2-bromo-3-methyl-5-nitropyridine product as an orange solid (99%).

Workup

  1. customThe vessel was capped with a septum
  2. additionwas added by syringe
  3. customThe septum cap
  4. customcap
  5. temperatureThe mixture was cooled to room temperature
  6. extractionextracted with toluene (3×)
  7. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5404c3f467f74576a0a014c0987fa628
Source dataset
uspto-grants-2016_03
Patent number
US09290526B2

Linked notes

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