Phosphorus oxychloride → 6-Bromo-2-chloroquinazoline

HRID 524080Notes

Reaction equation

HRID 524080 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](O)[N:6]=[CH:5]2.P(Cl)(Cl)([Cl:15])=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:15])[N:6]=[CH:5]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517410HCID 178517410, compound

Product 1

HCID 179135596-Bromo-2-chloroquinazolineYield 87%

Procedure

A solution of 6-bromoquinazolin-2-ol (9.72 g, 40 mmol) in phosphorus oxychloride (100 mL) was refluxed for 5 h. LCMS showed the reaction was completed. The reaction was cooled to RT, and most of phosphorus oxychloride was removed under reduced pressure. The residue was dropwise added to ice water (500 mL), and the resulting precipitate was collected by the filtration to give the title compound (9 g, 87%) as a yellow solid. MS (ES+) C8H3BrClFN2 requires: 260, 262. found: 261, 263 [M+H]+.

Workup

  1. custommost of phosphorus oxychloride was removed under reduced pressure
  2. additionThe residue was dropwise added to ice water (500 mL)
  3. filtrationthe resulting precipitate was collected by the filtration

Sources & evidence

ORD record
ord-d3e4c7cb6b9b4efa9c373e221090e763
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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