Phosphorus oxychloride → 6-Bromo-4-chloroquinoline

HRID 852984Notes

Reaction equation

HRID 852984 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2O.P(Cl)(Cl)([Cl:15])=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[Cl:15]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1785163796-Bromo-1,4-dihydroquinolin-4-one

Product 1

HCID 51395376-Bromo-4-chloroquinolineYield 98.5%

Procedure

The solid 6-bromo-quinolin-4-ol (52 g, 232.1 mmol) was added to phosphorus oxychloride (213.5 mL) and then the mixture was heated to reflux for 6 h to afford a light brown solution. After cooling to room temperature, the excess phosphorus oxychloride was removed under the vacuum. The remaining residue was poured into an ice-containing beaker (2 L). Then, it was slowly neutralized with solid potassium carbonate and the resulting solids were collected by filtration and washed with water. After drying in air, 55.46 g (98.5% yield) of 6-bromo-4-chloro-quinoline was isolated as a light yellow solid: EI-HRMS m/e calcd for C9H5BrClN (M+) 240.9294, found 240.9297.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 6 h
  3. customto afford a light brown solution
  4. customthe excess phosphorus oxychloride was removed under the vacuum
  5. additionThe remaining residue was poured into an ice-
  6. additioncontaining beaker (2 L)
  7. filtrationthe resulting solids were collected by filtration
  8. washwashed with water
  9. customAfter drying in air

Sources & evidence

ORD record
ord-615cab2696fc4f9bae4cf398fa7e94d2
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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