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
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 then heated to 110° C. for 4 hr. At the end of this time the reaction was cooled to room temperature and water cautiously added dropwise until all of the POCl3 was consumed. The product crystallised from the water and the solids were collected by filtration. The solids were washed with water and placed in a 250 mL Erlenmeyer where they were then triturated with water. After collection by filtration, washing with water, and drying in a vacuum oven, 4.6 g (84%) of the pure product was obtained.
Workup
- customInto a 500 mL three-neck round-bottom flask equipped with a condenser, magnetic stirrer and nitrogen inlet
- temperatureAt the end of this time the reaction was cooled to room temperature
- customwas consumed
- customThe product crystallised from the water
- filtrationthe solids were collected by filtration
- washThe solids were washed with water
- customwere then triturated with water
- customAfter collection
- filtrationby filtration
- washwashing with water
- customdrying in a vacuum oven
Sources & evidence
- ORD record
- ord-a3eb5f7466334e839f8905e60707b7bc
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07348340B2
Reaction notes
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