Thionyl Chloride → 5-Bromo-2-(chloromethyl)pyridine hydrochloride

HRID 640211Notes

Reaction equation

HRID 640211 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.S(Cl)([Cl:12])=O>C1(C)C=CC=CC=1>[ClH:12].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][Cl:12])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 5200169(5-Bromopyridin-2-yl)methanol

Product 1

HCID 534382005-Bromo-2-(chloromethyl)pyridine hydrochlorideYield 69.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a toluene (20.0 mL) solution of (5-bromo-pyridin-2-yl)-methanol (4.70 g, 25.0 mmol) described in Manufacturing Example 54-1-1 was added dropwise thionyl chloride (3.65 mL, 50.1 mmol) on an ice bath (0° C.) under nitrogen atmosphere, which was stirred for 5 minutes at room temperature. The solvent was evaporated under a reduced pressure to obtain the title compound (4.2 g, 69.2%) as a hydrochloride.

Workup

  1. customThe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-82af952401b4458e91b9b8c2306b61cf
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

Loading…