Phosphorus oxychloride → HCID 11209906, compound

HRID 1394122Notes

Reaction equation

HRID 1394122 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH:6]=[C:5]2O.P(Cl)(Cl)([Cl:22])=O>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH:6]=[C:5]2[Cl:22]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 178515591HCID 178515591, compound

Product 1

HCID 11209906HCID 11209906, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Into a 500 mL three-neck round-bottom flask equipped with a condenser, magnetic stirrer and nitrogen inlet was placed 5.2 g (16.3 mmoles) of 6-bromo-2-(3-fluorophenyl)-quinolin-4-ol. To this was added 15.2 mL (25.0 g, 163 mmoles, 10 equiv.) of phosphorus oxychloride with stirring. The mixture was heated to 110° C. for 4 hr. At the end of this time the reaction was cooled to room temperature and water was cautiously added dropwise until all of the POCl3 was consumed. The product crystallised from the water and solids were collected by filtration. The solids were washed with water, placed in a 250 mL Erlenmeyer and triturated with water. After collection by filtration, washing with water, and drying in a vacuum oven, 4.6 g (84%) of the product was obtained.

Workup

  1. customInto a 500 mL three-neck round-bottom flask equipped with a condenser, magnetic stirrer and nitrogen inlet
  2. temperatureAt the end of this time the reaction was cooled to room temperature
  3. customwas consumed
  4. customThe product crystallised from the water and solids
  5. filtrationwere collected by filtration
  6. washThe solids were washed with water
  7. customtriturated with water
  8. customAfter collection
  9. filtrationby filtration
  10. washwashing with water
  11. customdrying in a vacuum oven

Sources & evidence

ORD record
ord-0da39ba2d4fc4ea09006792ba0988364
Source dataset
uspto-grants-2008_03
Patent number
US07348340B2

Reaction notes

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