Thionyl Chloride → 2-Bromo-6-(chloromethyl)pyridine

HRID 1716499Notes

Reaction equation

HRID 1716499 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]O)[N:3]=1.S(Cl)([Cl:12])=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][Cl:12])[N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 3517811(6-Bromopyridin-2-yl)methanol

Product 1

HCID 216984342-Bromo-6-(chloromethyl)pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Bromo-6-hydroxymethylpyridine (5.00 g, 25.5 mmol) was dissolved in chloroform (30 ml) and thionyl chloride (2.8 ml, 38.3 mmol) was added, and the mixture was stirred at room temperature for 3 hours. After the reaction solution was concentrated, a saturated aqueous sodium bicarbonate was added to the residue and the precipitates were collected by filtration. After washing with water, the precipitates were dried in vacuo to give the title compound (5.20 g, 99%).

Workup

  1. concentrationAfter the reaction solution was concentrated
  2. additiona saturated aqueous sodium bicarbonate was added to the residue
  3. filtrationthe precipitates were collected by filtration
  4. washAfter washing with water
  5. customthe precipitates were dried in vacuo

Sources & evidence

ORD record
ord-2b745903f2e04dd4b4b4a5ca9f3cc4ab
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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