3,5-Dimethylpyridin-1-ium-1-olate → 4-Bromo-3,5-dimethylpyridin-1-ium-1-olate

HRID 75235Notes

Reaction equation

HRID 75235 reaction equation
[CH3:1][C:2]1[CH:3]=[N+:4]([O-:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Tl+3].[Br:23]Br>C(O)(=O)C>[Br:23][C:7]1[C:6]([CH3:8])=[CH:5][N+:4]([O-:9])=[CH:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 194853,5-Dimethylpyridin-1-ium-1-olateHCID 24408BromineHCID 21915946Thallium (III) acetate

Product 1

HCID 124930364-Bromo-3,5-dimethylpyridin-1-ium-1-olateYield 54%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3,5-dimethylpyridine 1-oxide (6.1 g, 50 mmol) in acetic acid (30 mL) was added thallium(III) triacetate (5.0 g, 13 mmol) and bromine (2.6 mL, 50 mmol). The resulting solution was heated at 60° C. overnight. The reaction was concentrated in vacuo, diluted with water and ethyl acetate. The organic layer was concentrated and residue was purified by silica gel chromatography to afford the desired product (5.40 g, 54%). 1H NMR (400 MHz, CDCl3): δ 7.96 (s, 2 H), 2.38 (s, 6 H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with water and ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. customresidue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c59f126bcb7d477aa23bf78153c778de
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Reaction notes

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