Phosphorus oxychloride → 5-Bromo-2-chloronicotinonitrile

HRID 2214740Notes

Reaction equation

HRID 2214740 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]#[N:10])[C:5](=O)[NH:6][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:12].O=P(Cl)(Cl)Cl>>[Br:1][C:2]1[CH:7]=[N:6][C:5]([Cl:12])=[C:4]([CH:3]=1)[C:9]#[N:10]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 72048705-Bromo-2-hydroxypyridine-3-carbonitrile

Product 1

HCID 219482695-Bromo-2-chloronicotinonitrile

Procedure

5-Bromo-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (33 g, 166 mmol) was added to a suspension of PCl5 (96.6 g, 464 mmol) in POCl3 (20 ml, 216 mmol). The mixture was stirred at reflux for 3 hours, cooled to room temperature and then poured slowly into ice/water. The resulting solid was fitered, washed with water, and dried in vacuo to afford the title compound.

Workup

  1. temperatureat reflux for 3 hours
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-fc0eb2507979454893822ed82cb73a52
Source dataset
uspto-grants-2006_09
Patent number
US07109199B2

Reaction notes

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