Boron tribromide → 1-(3-Bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone
Reaction equation
[Br:1][C:2]1[C:3]([O:13]C)=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[C:3]([OH:13])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a mixture of 1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone (1.0 g, 3.6 mmol) in methylene chloride (20 mL) was added 1.0 M boron tribromide in methylene chloride (3.8 mL, 3.8 mmol) at −78° C. After stirring at −78° C. for 10 minutes, the reaction was allowed to warm to 0° C. and was then quenched with water at 0° C. and extracted with dichloromethane. The combined organic layers were washed with brine and dried over sodium sulfate. The volatiles were removed under reduced pressure to afford 1-(3-Bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone (0.91 g, 96%). 1H NMR (CDCl3, 300 MHz) δ 12.96 (1H, s), 7.72 (1H, s), 2.64 (3H, s), 2.59 (3H, s) ppm.
Workup
- temperatureto warm to 0° C.
- customwas then quenched with water at 0° C.
- extractionextracted with dichloromethane
- washThe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- customThe volatiles were removed under reduced pressure
Sources & evidence
- ORD record
- ord-4329c47b22574369a831c0363746a17d
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096600B2
Reaction notes
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