Thionyl Chloride → 5-Bromo-2-chloronicotinic acid

HRID 4794Notes

Reaction equation

HRID 4794 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(Cl)([Cl:14])=O>CN(C)C=O>[Br:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([Cl:14])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178418525HCID 178418525, compound

Product 1

HCID 27633425-Bromo-2-chloronicotinic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 15 g (0.069 mole) of 5-bromo-2-hydroxy nicotinic acid was added 75 ml of thionyl chloride and 3 ml of dimethylformamide. The mixture was heated to reflux for 30 minutes. After cooling, the excess thionyl chloride was removed by rotary evaporation and the residue poured into water (1 liter) with vigorous agitation. The precipitate was collected and the mother liquor condensed to 1/2 the volume, yielding additional precipitate. The precipitates were combined and crystallized from toluene giving 6 g (37%) of material. The product was recrystallized from toluene, m.p. 174°-177° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. temperatureAfter cooling
  4. customthe excess thionyl chloride was removed by rotary evaporation
  5. additionthe residue poured into water (1 liter) with vigorous agitation
  6. customThe precipitate was collected
  7. customthe mother liquor condensed to 1/2 the volume
  8. customyielding additional precipitate
  9. customcrystallized from toluene giving 6 g (37%) of material
  10. customThe product was recrystallized from toluene, m.p. 174°-177° C.

Sources & evidence

ORD record
ord-1c2ca15851eb4519b4b2de95c0278d64
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Reaction notes

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