2,3-Lutidine → 5-BROMO-2,3-DIMETHYLPYRIDINE

HRID 391086Notes

Reaction equation

HRID 391086 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH3:7])[C:2]=1[CH3:8].[Br:9]Br.[OH-].[Na+]>S(=O)(=O)(O)O>[Br:9][C:5]1[CH:4]=[C:3]([CH3:7])[C:2]([CH3:8])=[N:1][CH:6]=1

Participants

5

Reactant 3

HCID 114202,3-LutidineHCID 14798Sodium HydroxideHCID 24408Bromine

Product 1

HCID 114467625-BROMO-2,3-DIMETHYLPYRIDINE

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
155 °C

Procedure

To a solution of 2,3-lutidine (0.51 mL) in fuming sulfuric acid (10 mL) at 155° C. was added bromine (0.3 mL) dropwise over 2 h. The reaction mixture was then heated at 155° C. for 16 h. After cooling to room temperature, the mixture was poured onto ice and the ph adjusted to 10 with aqueous sodium hydroxide solution. The product was extracted into ethylacetate (3×40 mL) and the organic layers were dried (MgSO4), reduced in vacuo and purified on silica to give 5-bromo-2,3-dimethyl-pyridine as a yellow oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe mixture was poured onto ice
  3. extractionThe product was extracted into ethylacetate (3×40 mL)
  4. dry with materialthe organic layers were dried (MgSO4)
  5. custompurified on silica

Sources & evidence

ORD record
ord-82f4b222e80a471b9a25fca2e9a1d937
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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