Potassium Hydroxide → 4-Bromo-2,6-dimethylpyridine

HRID 1038064Notes

Reaction equation

HRID 1038064 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6](O)[CH:5]=[C:4]([CH3:9])[N:3]=1.P(Br)(Br)([Br:12])=O.[OH-].[K+]>C(Cl)(Cl)Cl>[Br:12][C:6]1[CH:7]=[C:2]([CH3:1])[N:3]=[C:4]([CH3:9])[CH:5]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24613Phosphorus oxybromideHCID 178429033HCID 178429033, compound

Product 1

HCID 130817354-Bromo-2,6-dimethylpyridineYield 220.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

2,6-Dimethyl-pyridin-4-ol 10I (6.16 g, 50 mmol), PBr5 (11.9 g, 27.65 mmol) and POBr3 (2.5 mL, 24.6 mmol) was combined and CHCl3 (2.5 mL) was added. The reaction was heated at 100° C. for 5 hrs and then cooled in an ice bath. Solid KOH was added till PH reached 7-8 followed by extraction with Et2O (3×75 mL). The combined ether layer was dried and evaporated in vacuo to give a thick clear crude oil (10.1 g) as the title compound.

Workup

  1. temperaturecooled in an ice bath
  2. extractionfollowed by extraction with Et2O (3×75 mL)
  3. dry with materialThe combined ether layer was dried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-0fe995f212544c3883ed858beb75cc27
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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