Methanol → Methyl 5-bromopyridine-2-carboxylate

HRID 474197Notes

Reaction equation

HRID 474197 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.OS(O)(=O)=O.[CH3:16]O>C(Cl)Cl>[CH3:16][O:9][C:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[O:10]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 1118Sulfuric AcidHCID 6085445-Bromopyridine-2-carboxylic acid

Product 1

HCID 7016458Methyl 5-bromopyridine-2-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromo-2-pyridine carboxylic acid (26.2 g, 0.124 mol) and conc. H2SO4 (12.5 mL) in MeOH (250 mL) was heated to 60° C. and diluted with additional MeOH (250 mL). After 18 h at 60° C., the mixture was cooled to rt, diluted with DCM, and washed with a solution consisting of 21 g KOH in 200 mL water, sat. K2CO3, and water. The organic layer was dried and concentrated to give the title compound (21.4 g, 76%) as a white solid. This material was used in the next step without further purification.

Workup

  1. temperaturethe mixture was cooled to rt
  2. washwashed with a solution
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a8c7201af5bf40b6acd6927c4e96eaf1
Source dataset
uspto-grants-2014_01
Patent number
US08637520B2

Reaction notes

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