4-Hydroxymethylpyridine → 4-(Bromomethyl)pyridine hbr

HRID 2186481Notes

Reaction equation

HRID 2186481 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7]O)=[CH:3][CH:2]=1.P(Br)(Br)(Br)(Br)[Br:10]>C(Cl)(Cl)Cl>[BrH:10].[Br:10][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 114724-HydroxymethylpyridineHCID 62678Phosphorus pentabromide

Product 1

HCID 127522194-(Bromomethyl)pyridine hbrYield 233.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-pyridylcarbinol (3 g, 27.5 mmol) in 30 mL of CHCl3 was added phosphorus pentabromide (5.93 g, 13.7 mmol). The solution was refluxed for 1 hour. The solvent was removed in vacuo and recrystallized in ethanol to afford the title compound as a white solid (4.05 g, 58.1%). ES (+) MS m/e=173 (M+H).

Workup

  1. temperatureThe solution was refluxed for 1 hour
  2. customThe solvent was removed in vacuo
  3. customrecrystallized in ethanol

Sources & evidence

ORD record
ord-2ebdddc665ae45d488ee7f781bfa1fc8
Source dataset
uspto-grants-2002_06
Patent number
US06403792B1

Reaction notes

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