Phosphorus oxychloride → 6-Bromo-2-chloro-5-fluoroquinazoline

HRID 56478Notes

Reaction equation

HRID 56478 reaction equation
[Br:1][C:2]1[C:3]([F:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](O)[N:6]=[CH:5]2.P(Cl)(Cl)([Cl:16])=O>>[Br:1][C:2]1[C:3]([F:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:16])[N:6]=[CH:5]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1785175476-bromo-5-fluoroquinazolin-2(1H)-one

Product 1

HCID 574611366-Bromo-2-chloro-5-fluoroquinazoline

Procedure

A solution of 6-bromo-5-fluoroquinazolin-2-ol (3.0 g, 12.34 mmol) in phosphoryl trichloride (10 mL) was refluxed at 135° C. for 5 hours. Most of phosphoryl trichloride was removed under reduced pressure, and the residue was dropwise added to ice water (200 mL). The resulting precipitate was collected via filtration as a yellow solid (3.1 g, 96%). MS (ES+) C8H3BrClFN2 requires: 260, found: 261, 263 [M+H]+.

Workup

  1. customMost of phosphoryl trichloride was removed under reduced pressure
  2. additionthe residue was dropwise added to ice water (200 mL)
  3. filtrationThe resulting precipitate was collected via filtration as a yellow solid (3.1 g, 96%)

Sources & evidence

ORD record
ord-553c038ce2194e5d9578df75645dda80
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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