Methanol → 3-Fluoro-2-methylquinolin-7-ol hydrobromide

HRID 339094Notes

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:16].CO>C(Cl)Cl>[BrH:16].[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]=2

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-fluoro-7-methoxy-2-methylquinoline (0.255 g, 1.33 mmol) in DCM (5 mL) was added BBr3 (6.67 mL, 6.67 mmol) at 0° C. The mixture was stirred at 0° C. for 2 hours and at ambient temperature for 3 hours. Methanol (10 mL) was added slowly and the resulting mixture was stirred at ambient temperature for 1 hour. The solvent was removed under reduced pressure. The resulting solid was suspended in 1:1 ether/hexane and stirred at ambient temperature for 10 minutes. The solid was collected by filtration to give 3-fluoro-2-methylquinolin-7-ol hydrobromide (0.37 g, 1.43 mmol, 107% yield) as a solid.

Workup

stirringthe resulting mixture was stirred at ambient temperature for 1 hour
customThe solvent was removed under reduced pressure
stirringstirred at ambient temperature for 10 minutes
filtrationThe solid was collected by filtration

Sources & evidence

ORD record: ord-7a67529caee94fde97e6ff41eda3e59c
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889704B2

Reaction notes

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