Phosphorus oxychloride → 6-Bromo-2-chloro-7-methoxyquinazoline

HRID 524074Notes

Reaction equation

HRID 524074 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7](O)[N:6]=[CH:5]2.P(Cl)(Cl)([Cl:17])=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([Cl:17])[N:6]=[CH:5]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178486882HCID 178486882, compound

Product 1

HCID 591992766-Bromo-2-chloro-7-methoxyquinazolineYield 75%

Procedure

To a solution of 6-bromo-7-methoxyquinazolin-2-ol (3.0 g, 11.8 mmol) in phosphoryl trichloride (30 mL) was refluxed at 130° C. for 5 h. LCMS showed the reaction was completed. The reaction was cooled to RT, and most of phosphoryl trichloride was evaporated. The residue was dropwise added to ice water (100 mL), and the resulting precipitate was collected via filtration to give the title compound as a yellow solid (2.4 g, 75%). MS (ES+) C9H6BrClN2O requires: 272, 274. found: 273, 275 [M+H]+.

Workup

  1. custommost of phosphoryl trichloride was evaporated
  2. additionThe residue was dropwise added to ice water (100 mL)
  3. filtrationthe resulting precipitate was collected via filtration

Sources & evidence

ORD record
ord-64f13e311d0d4c8696675b67dc549d23
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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