Thionyl bromide → 4-(Bromomethyl)-2-methylpyridine

HRID 1183834Notes

Reaction equation

HRID 1183834 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][N:3]=1.S(Br)([Br:12])=O>ClCCl>[Br:12][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 68176Thionyl bromideHCID 9942144(2-Methylpyridin-4-yl)methanol

Product 1

HCID 533995404-(Bromomethyl)-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-methylpyridin-4-yl)-methanol (0.510 g, 4.14 mmol) in 8 mL of dichloromethane was added thionyl bromide (1.03 g, 4.97 mmol) dropwise. After 1 h, the reaction was quenched with saturated aqueous ammonium chloride. The organic solution was washed 2× with water, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 4-(bromomethyl)-2-methylpyridine that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 188.0 (81Br) for [M+H]+.

Workup

  1. customthe reaction was quenched with saturated aqueous ammonium chloride
  2. washThe organic solution was washed 2× with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-309a4a11c4b9439e833cae1f9021342d
Source dataset
uspto-grants-2014_03
Patent number
US08664387B2

Reaction notes

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