Phosphorus oxychloride → 6-Bromo-2-chloroquinazoline

HRID 2274179Notes

Reaction equation

HRID 2274179 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

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 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

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

Sources & evidence

ORD record
ord-99daa358aa0e4bb384404a0033d7ade4
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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