Methanol → 3-Fluoro-7-hydroxy-2-methylquinoline
Reaction equation
[F:1][C:2]1[C:3]([CH3:14])=[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[C:3]([CH3:14])=[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-methoxy-2-methylquinoline (0.16 g, 0.85 mmol) was taken up in dichloromethane (4 ml) under nitrogen and treated with boron tribromide solution (4 ml of a 1.0M solution in dichloromethane, 4.0 mmol). The reaction was stirred for 24 hours at ambient temperature followed by the slow addition of excess methanol. The solution was stirred for a further 2 hours and then evaporated to dryness to give 3-fluoro-7-hydroxy-2-methylquinoline which was used without further purification.
Workup
- stirringThe solution was stirred for a further 2 hours
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-1671a113e0e84df59dd109665832c08a
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492560B2
Reaction notes
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