Thionyl Chloride → 5-(Chloromethyl)-2-methylpyridine

HRID 2361699Notes

Reaction equation

HRID 2361699 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][CH:3]=1.S(Cl)([Cl:12])=O>ClCCl>[Cl:12][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[N:7][CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11228788(6-Methylpyridin-3-yl)methanol

Product 1

HCID 122143385-(Chloromethyl)-2-methylpyridineYield 125.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (6-methyl-3-pyridinyl)methanol (166 mg, 1.35 mmol) in dichloromethane (10 ml) was added thionyl chloride (108 μl, 1.48 mmol) giving a colourless solution. After 30 minutes the mixture was concentrated giving a brown solid (240 mg, quant. yield) that was used directly in the next step without purification.

Workup

  1. customgiving a colourless solution
  2. concentrationAfter 30 minutes the mixture was concentrated

Sources & evidence

ORD record
ord-ff65268ec65140338165f7b36867f984
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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