Phosphorus oxychloride → HCID 11209906, compound
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
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
6-Bromo-2-(3-fluorophenyl)-quinolin-4-ol (5.2 g, 16.3 mmoles) was placed in a 500 mL three-neck round-bottom flask equipped with a condenser, magnetic stirrer and nitrogen inlet. 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. Material 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
- customequipped with a condenser, magnetic stirrer and nitrogen inlet
- temperatureAt the end of this time the reaction was cooled to room temperature
- customwas consumed
- customMaterial crystallised from the water and solids
- filtrationwere collected by filtration
- washThe solids were washed with water
- customtriturated with water
- customAfter collection
- filtrationby filtration
- washwashing with water
- customdrying in a vacuum oven
Sources & evidence
- ORD record
- ord-772f0f0387a94133a64ca52698573a60
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06906193B2
Reaction notes
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