Dimethylformamide → 5-Bromonicotinoyl chloride

HRID 2041799Notes

Reaction equation

HRID 2041799 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].CN(C)C=O.S(Cl)([Cl:18])=O>>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([Cl:18])=[O:8]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 887075-Bromonicotinic acid

Product 1

HCID 27812235-Bromonicotinoyl chloride

Procedure

To a mixture of 5-bromonicotinic acid (10 g) in thionyl chloride (25 mL) was added anhydrous dimethylformamide (DMF) (0.5 mL). The whole was heated to reflux for overnight. After cooling to RT, the excess thionyl chloride was removed under reduced pressure. A white solid (3) (11 g) was obtained, which was used for the next step without further purification.

Workup

  1. temperatureThe whole was heated
  2. temperatureto reflux for overnight
  3. customthe excess thionyl chloride was removed under reduced pressure

Sources & evidence

ORD record
ord-34b76b4d9aec4116a60692cb33427d3c
Source dataset
uspto-grants-2013_11
Patent number
US08585926B2

Reaction notes

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