Phosphorus oxychloride → HCID 89782123, compound

HRID 1056047Notes

Reaction equation

HRID 1056047 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=O)[C:8]([C:13]([F:16])([F:15])[F:14])=[N:7]2.O=P(Cl)(Cl)[Cl:19]>>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:19])[C:8]([C:13]([F:16])([F:15])[F:14])=[N:7]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 89783720HCID 89783720, compound

Product 1

HCID 89782123HCID 89782123, compoundYield 52%

Procedure

A solution of 8-bromo-3-(trifluoromethyl)quinoxalin-2(1H)-one (432.0 mg, 1.474 mmol) in POCl3 (5.0 mL) was heated at reflux for 10 h then at 100° C. for 2.5 d, then at 140° C. for 10 h. Excess POCl3 was removed in vacuo, and the residue was taken up in DCM (60 mL) and transferred to an Erlenmeyer flask before saturated aq. NaHCO3 (40 mL) was added cautiously (over 5 min) with rapid stirring. The resulting biphasic mixture was stirred rapidly for 5 min (some gas evolution), and the organic layer was separated. The aq. layer was extracted with DCM (3×20 mL), and all organic layers were combined, dried over Na2SO4, filtered, and concentrated in vacuo to provide 5-bromo-3-chloro-2-(trifluoromethyl)quinoxaline (224c, 52%). MS (ESI, pos. ion) m/z: 310.9 (M+1).

Workup

  1. temperatureat reflux for 10 h
  2. waitat 140° C. for 10 h
  3. customExcess POCl3 was removed in vacuo
  4. additionwas added cautiously (over 5 min) with rapid stirring
  5. customwas separated
  6. extractionThe aq. layer was extracted with DCM (3×20 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b77a25f140447419810166078fddc3f
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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