Bromine → 5-Bromo-7-chloro-2-methylquinolin-6-ol
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][C:3]=1[OH:13].[Br:14]Br>C(O)(=O)C>[Br:14][C:4]1[C:3]([OH:13])=[C:2]([Cl:1])[CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 7-chloro-2-methylquinolin-6-ol (1C) (450 mg, 2.3 mmol) in acetic acid (15 mL) was added Br2 (0.13 mL, 2.4 mmol) at ambient temperature. The mixture was stirred at ambient temperature for 2 hours. The solid that formed was filtered and collected to give 1D as an off-white solid as the HBr salt (847 mg, 100%). LCMS-ESI+ (m/z): 281.1, 283.1 (M+H)+.
Workup
- customThe solid that formed
- filtrationwas filtered
- customcollected
Sources & evidence
- ORD record
- ord-004a15b9a8ca4b57a25185195e3b21ed
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296758B2
Reaction notes
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