Dimethylformamide → 7-Bromo-2-chloroquinoxaline

HRID 929344Notes

Reaction equation

HRID 929344 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8](=O)[NH:9]2)=[CH:4][CH:3]=1.CN(C=O)C.O=P(Cl)(Cl)[Cl:20]>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([Cl:20])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 49132647-bromo-1H-quinoxalin-2-one

Product 1

HCID 49132537-Bromo-2-chloroquinoxalineYield 75%

Conditions

Temperature
120 °C

Procedure

To a suspension of 7-bromoquinoxalin-2(1H)-one (224 g, 1 mol, 1.0 eq.) in POCl3 (1000 mL) was added DMF (3.65 g, 0.05 mol, 0.05 eq.). The resulting mixture was stirred at 120° C. for 2 h, then cooled to rt and slowly poured into ice-water with vigorous stirring. The precipitate was collected by filtration and dried to afford 7-bromo-2-chloroquinoxaline as brown solid (180 g, 75%).

Workup

  1. temperaturecooled to rt
  2. filtrationThe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-2878f472b3044e1e9d10ced818ca33c5
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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