Phosphorus oxychloride → 6-Bromo-1-chlorophthalazine

HRID 454859Notes

Reaction equation

HRID 454859 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](O)=[N:7][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)[C:8]([Cl:15])=[N:7][N:6]=[CH:5]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178518884HCID 178518884, compound

Product 1

HCID 220304246-Bromo-1-chlorophthalazine

Conditions

Temperature
105 °C

Procedure

A mixture of 6-bromophthalazin-1-ol (10.0 g, 44.4 mmol) in phosphorus oxychloride (104 mL, 1111 mmol) was heated at 105° C. in an oil bath for 3 h. After cooling to RT, the volatiles were removed by vacuum distillation. The residue was diluted with CH2Cl2 and treated with 10% Na2CO3 solution. After stirring for 3 h, the mixture was diluted with 10% Na2CO3 and extracted with CH2Cl2 (3×). The combined organic solution was dried over Na2SO4, filtered through a short pad of silica gel, eluted with EtOAc, and concentrated in vacuo to yield the title compound as a tan solid. MS (ESI, pos. ion) m/z: 242.9, 244.9 (M+1).

Workup

  1. temperatureAfter cooling to RT
  2. customthe volatiles were removed by vacuum distillation
  3. additionThe residue was diluted with CH2Cl2
  4. additiontreated with 10% Na2CO3 solution
  5. additionthe mixture was diluted with 10% Na2CO3
  6. extractionextracted with CH2Cl2 (3×)
  7. dry with materialThe combined organic solution was dried over Na2SO4
  8. filtrationfiltered through a short pad of silica gel
  9. washeluted with EtOAc
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-646dd27e36ec418dbaf940afabbc88d7
Source dataset
uspto-grants-2013_07
Patent number
US08497269B2

Reaction notes

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