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

HRID 1043485Notes

Reaction equation

HRID 1043485 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, 2H), 2.38 (s, 6H).

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-7c97cd6c01c04e279eb3c1a7285f9f93
Source dataset
uspto-grants-2013_10
Patent number
US08563541B2

Reaction notes

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