Phosphorus oxychloride → 6-Bromo-2-chloroquinazoline

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.O=P(Cl)(Cl)[Cl:15]>>[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

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178517410HCID 178517410, compound

Product 1

HCID 179135596-Bromo-2-chloroquinazoline

Procedure

A solution of 6-bromoquinazolin-2-ol (31) (6.0 g, 26.7 mmol) in POCl3 (80 mL) was refluxed at 110° C. for 5 hours. An aliquot of the reaction mixture was analyzed by LCMS and indicated that the reaction had proceeded to completion. Most of POCl3 was removed under reduced pressure, and the residue was added dropwise to ice water (500 mL). The resulting precipitate was collected via filtration as a yellow solid (3.5 g, 54%). MS (ES+) C8H4BrClN2 requires: 242. found: 243, 245 [M+H]+.

Workup

customMost of POCl3 was removed under reduced pressure
additionthe residue was added dropwise to ice water (500 mL)
filtrationThe resulting precipitate was collected via filtration as a yellow solid (3.5 g, 54%)

Sources & evidence

ORD record: ord-25992e7f8ead4927aa58d8dd9cb79fc0
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340514B2

Reaction notes

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