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

HRID 1774909Notes

Reaction equation

HRID 1774909 reaction equation
[Cl: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]([Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 68176Thionyl bromideHCID 7062237(2-Chloropyridin-4-yl)methanol

Product 1

HCID 129548074-(Bromomethyl)-2-chloropyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloropyridine-4-methanol (1.02 g, 7.10 mmol) in 15 mL of dichloromethane was added thionyl bromide (1.77 g, 8.53 mmol) dropwise. After 15 min, 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-chloropyridine that gave a mass ion (ES+) of 208.0 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-3fb61f897cb34684b490560ebf7bcbe7
Source dataset
uspto-grants-2016_02
Patent number
US09260418B2

Reaction notes

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