Boron tribromide → 2,2-Difluoro-1-(2-fluoro-4-hydroxyphenyl)ethan-1-one
Reaction equation
[F:1][CH:2]([F:14])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11]C)=[CH:7][C:6]=1[F:13])=[O:4].B(Br)(Br)Br>C(Cl)Cl>[F:14][CH:2]([F:1])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[F:13])=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To 2,2-difluoro-1-(2-fluoro-4-methoxyphenyl)ethanone (45.0 g, 0.22 mol) in 400 mL of CH2Cl2 at −78° C. was added BBr3 (165.67 g, 0.66 mol) in 100 mL of CH2Cl2 dropwise. The resulting solution was stirred overnight at 25° C., and was quenched by dropwise addition of CH3OH (900 mL) at −30° C. and after stirring for 2 hours at −30° C. and for 1 hour at 25° C., the solvents were evaporated and the residue was purified by column chromatography (PE/EA 6:1) to afford 2,2-difluoro-1-(2-fluoro-4-hydroxyphenyl)ethanone as a solid.
Workup
- customwas quenched by dropwise addition of CH3OH (900 mL) at −30° C.
- stirringafter stirring for 2 hours at −30° C. and for 1 hour at 25° C.
- customthe solvents were evaporated
- customthe residue was purified by column chromatography (PE/EA 6:1)
Sources & evidence
- ORD record
- ord-b38583673d8e4a07986fd872f6f200a2
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193228B2
Reaction notes
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