Hydrogen Bromide → 3-(Bromomethyl)pyridine hydrobromide

HRID 2186482Notes

Reaction equation

HRID 2186482 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7]O)[CH:2]=1.[BrH:9]>CCOC(C)=O>[BrH:9].[Br:9][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 75103-Pyridinemethanol

Product 1

HCID 127070373-(Bromomethyl)pyridine hydrobromideYield 122.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 3-pyridylcarbinol (2 g, 18.3 mmol) was added 47-49% hydrobromic acid (2 mL, 13.7 mmol). The solution was refluxed for 3 hours. The solution was diluted with EtOAc and extracted thrice with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give a solid. The solid was recrystallized in ethanol to afford the title compound as a white solid (2.13 g, 45.8%). ES (+) MS m/e=173 (M+H).

Workup

  1. temperatureThe solution was refluxed for 3 hours
  2. extractionextracted thrice with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a solid
  7. customThe solid was recrystallized in ethanol

Sources & evidence

ORD record
ord-7bf26b5b5b434939bce726683021e564
Source dataset
uspto-grants-2002_06
Patent number
US06403792B1

Reaction notes

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