Thionyl Chloride → 5-Bromo-2-chloronicotinic acid

HRID 1047144Notes

Reaction equation

HRID 1047144 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([OH:11])=[O:10])[C:5](O)=[N:6][CH:7]=1.S(Cl)([Cl:14])=O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([OH:11])=[O:10])[C:5]([Cl:14])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178418525HCID 178418525, compound2×

Product 1

HCID 27633425-Bromo-2-chloronicotinic acidYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5-bromo-2-hydroxypyridine-3-carboxylic acid (Intermediate 10, 14 g, 64.2 mmol) was added thionyl chloride (70 mL) and dimethylformamide (8 mL). The reaction mixture was heated to reflux for 3 h. After cooling, the excess thionyl chloride was removed by rotary evaporation and the residue was poured into water (1 L) and extracted with ethyl acetate (3×100 mL). The organic layer was dried over anhydrous sodium sulphate then filtered and concentrated to afford 7.0 g (47%) of 5-bromo-2-chloropyridine-3-carboxylic acid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 h
  3. temperatureAfter cooling
  4. customthe excess thionyl chloride was removed by rotary evaporation
  5. additionthe residue was poured into water (1 L)
  6. extractionextracted with ethyl acetate (3×100 mL)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  8. filtrationthen filtered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-20d316b94a914c76b7c5cd86dc396a31
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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