Methanol → Methyl 3-bromo-2-pyridinecarboxylate

HRID 272641

Reaction equation

HRID 272641 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

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 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.

Workup

  1. temperatureis reflux
  2. customto return to ambient temperature
  3. extractionIt is extracted 3 times with ethyl acetate
  4. customthe organic phase is dried on Na2SO4 and vacuum
  5. customevaporated

Sources & evidence

ORD record
ord-eca464055933479c9ffeff3ae11eeeaa
Source dataset
uspto-grants-2008_11
Patent number
US07456192B2

Linked notes

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