Methanol → 3-Fluoroquinolin-7-OL
Reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12]C)[CH:6]=2.B(Br)(Br)Br.CO>ClCCl>[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([OH:12])[CH:6]=2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Fluoro-7-methoxyquinoline (130 mg, 0.74 mmol) was taken up in dichloromethane (2 ml) under nitrogen and treated with boron tribromide (4 ml of a 1.0M solution of in dichloromethane). The reaction mixture was stirred for 24 hours at ambient temperature followed by quenching the reaction by the slow addition of excess methanol. The solution was stirred for a further 2 hours and evaporated to dryness to give 3-fluoro-7-hydroxyquinoline which was used without further purification.
Workup
- customby quenching
- customthe reaction
- stirringThe solution was stirred for a further 2 hours
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-9ecadf86ec4b4c428f8e3746328eae92
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492560B2
Reaction notes
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