Dimethylformamide → Methyl 6-bromopyridine-2-carboxylate

HRID 570979Notes

Reaction equation

HRID 570979 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:15]N(C=O)C>CO>[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:15])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 5939196-Bromopyridine-2-carboxylic acid

Product 1

HCID 16217886Methyl 6-bromopyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-bromo-2-pyridinecarboxylic acid (0.3 g, 1.5 mmol), thionyl chloride (0.27 ml, 3.7 mmol) and DMF (catalytic amount) in methanol (10 ml) was heated to reflux for 2 hrs under nitrogen atmosphere. The reaction mixture was concentrated to dryness to provide methyl 6-bromo-2-pyridinecarboxylate.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hrs under nitrogen atmosphere
  3. concentrationThe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-070d73fb33fb436b9b49bd1a86b57499
Source dataset
uspto-grants-2015_05
Patent number
US09024021B2

Reaction notes

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