Methanol → 5-Trifluoromethyl-pyridine-2-carboxylic acid methyl ester

HRID 927526Notes

Reaction equation

HRID 927526 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([C:9]([OH:11])=[O:10])=[N:7][CH:8]=1.S(Cl)(Cl)=O.[CH3:18]O>>[CH3:18][O:10][C:9]([C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:12])([F:1])[F:13])=[CH:8][N:7]=1)=[O:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 109103495-(trifluoromethyl)pyridine-2-carboxylic Acid

Product 1

HCID 189969195-Trifluoromethyl-pyridine-2-carboxylic acid methyl esterYield 84%

Procedure

A solution of 5-(trifluoromethyl)-pyridine-2-carboxylic acid (CAN 80194-69-0, 3 g, 15.7 mmol) and sulfurous dichloride (0.1 mL) in methanol (30 mL) was stirred under reflux conditions overnight. Removal of the solvent provided the crude title compound which was purified by column chromatography (silica gel, 20 g, 10% ethyl acetate in petroleum ether) to obtain the title compound (2.7 g, 84%) as white solid; MS (EI): m/e=206.1 [M+H]+.

Workup

  1. customRemoval of the solvent
  2. customprovided the crude title compound which
  3. customwas purified by column chromatography (silica gel, 20 g, 10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-d9f1ddcf6b314232a96dd47fab1f8e04
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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