Phosphorus oxychloride → 8-Bromo-2-chloroquinoxaline

HRID 216728Notes

Reaction equation

HRID 216728 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=O)[CH:8]=[N:7]2.O=P(Cl)(Cl)[Cl:15]>>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:15])[CH:8]=[N:7]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 593927088-Bromoquinoxalin-2(1H)-one

Product 1

HCID 593926708-Bromo-2-chloroquinoxaline

Conditions

Temperature
50 °C

Procedure

A mixture of 2.0 g (ca. 7.64 mmol) 8-Bromo-1H-quinoxalin-2-one and 36 ml of POCl3 is heated to 50° C. for 16 h. After cooling, the excess of POCl3 is evaporated, water is then added and extracted 3× with CH2Cl2. The combined organic layers are successively washed with water, NaHCO3, saturated brine, dried over Na2SO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography (silicagel, hexane:CH2Cl2=7:3=>1:1) to afford the title compound as a pale orange solid, MS: 243 (M)+

Workup

  1. temperatureAfter cooling
  2. customthe excess of POCl3 is evaporated
  3. additionwater is then added
  4. extractionextracted 3× with CH2Cl2
  5. washThe combined organic layers are successively washed with water, NaHCO3, saturated brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate is concentrated in vacuo
  9. customThe residue is purified by chromatography (silicagel, hexane:CH2Cl2=7:3=>1:1)

Sources & evidence

ORD record
ord-d17185f5bce94effaf1c9d3a0087e6ea
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

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