Boron tribromide → 3-Fluoro-4-methylphenol

Temperature

-70 °C

To a −70° C. solution of 3-fluoro-4-methyl anisole (1.62 g; 11.6 mmol) in CH2Cl2 (10 mL) was added dropwise BBr3 (10 mL; 12 mmol). The reaction mixture was stirred at −70° C. for 10 min, then allowed to warm to 0° C. and stirred at 0° C. for 2 h. The reaction was allowed to warm to RT and concentrated in vacuo and the residue was partitioned between H2O and EtOAc. The organic phase was washed with H2O, dried (Na2SO4) and concentrated in vacuo to give 3-fluoro-4-methyl phenol (1.1 g; 75%) as an oil.

1. temperatureto warm to 0° C.
2. stirringstirred at 0° C. for 2 h
3. temperatureto warm to RT
4. concentrationconcentrated in vacuo
5. customthe residue was partitioned between H2O and EtOAc
6. washThe organic phase was washed with H2O
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated in vacuo

ORD record

ord-be3ba95f315f4cc39d451cc115a70d5d

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07084162B2