Methanol → Methyl 3-bromo-2-pyridinecarboxylate

Reaction equation

[Br:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.O.[CH3:17]O>>[CH3:17][O:9][C:8]([C:3]1[C:2]([Br:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:10]

Participants

Reactant 4

HCID 887Methanol

HCID 962Water

HCID 1118Sulfuric Acid

HCID 20501293-Bromopyridine-2-carboxylic Acid

Product 1

HCID 12828946Methyl 3-bromo-2-pyridinecarboxylateYield 42%

Procedure

A mixture of 5.45 g of 3-bromo-2-pyridine carboxylic acid (27.0 mmol, 1 eq.), obtained in example 3b), in 100 ml of methanol is reflux heated in the presence of 8 ml of sulfuric acid. The reaction mixture is allowed to return to ambient temperature and poured into water. It is extracted 3 times with ethyl acetate, the organic phase is dried on Na2SO4 and vacuum evaporated. 2.48 g (42%) of esterified product is obtained.