Dimethylformamide → 5-Bromonicotinoyl chloride

HRID 2170597Notes

Reaction equation

HRID 2170597 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=O)C.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 DMF (0.5 ml). The whole was heated to reflux for overnight. After cooled to RT, the excess thionyl chloride was removed under reduced pressure. A white solid 5 (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-480f320f6a754834a05e1a0e6ccec54e
Source dataset
uspto-grants-2015_06
Patent number
US09051284B2

Reaction notes

Loading…