Phosphorus oxychloride → 6-Bromo-2,8-dichloroquinazoline

HRID 56451Notes

Reaction equation

HRID 56451 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[N:8]=[C:7](O)[N:6]=[CH:5]2.P(Cl)(Cl)([Cl:16])=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[N:8]=[C:7]([Cl:16])[N:6]=[CH:5]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517411HCID 178517411, compound

Product 1

HCID 591992946-Bromo-2,8-dichloroquinazoline

Procedure

A solution of 6-bromo-8-chloroquinazolin-2-ol (9.0 g, 35 mmol) in phosphorus oxychloride (100 mL) was refluxed for 5 hours. Most of phosphorus oxychloride was removed under reduced pressure, and the residue was added to a stirring ice water (500 mL). The resulting precipitate was collected via filtration and then refluxed in THF. The solid was filtered off, and the filtrate was concentrated to give the title compound a yellow solid (7.0 g, 78%). MS (ES+) C8H4BrClN2 requires: 275, 277, found: 276, 278 [M+H]+.

Workup

  1. customMost of phosphorus oxychloride was removed under reduced pressure
  2. additionthe residue was added to a stirring ice water (500 mL)
  3. filtrationThe resulting precipitate was collected via filtration
  4. temperaturerefluxed in THF
  5. filtrationThe solid was filtered off
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3021d1642a924a3094a3d1f0103b9154
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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