Reacción #43920

Ecuación de reacción

sodium thiosulfate

4-bromo-3,5-dimethylphenol

N-fluoropyridinium triflate

→

title compound

Rendimiento 36.2%

4-bromo-2-fluoro-3,5-dimethylphenol

Rendimiento 36.2%

Disolventes

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated
2. 2
   Temperaturaunder reflux for 7 hr
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe extract was washed successively with water and saturated brine
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70)

Procedimiento

To a solution of 4-bromo-3,5-dimethylphenol (2.00 g, 9.95 mmol) in 1,2-dichloroethane (20 mL) was added N-fluoropyridinium triflate (6.15 g, 24.9 mmol), and the mixture was heated under reflux for 7 hr. The reaction mixture was treated with 1 M aqueous sodium thiosulfate solution, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70) to give the title compound (0.790 g, yield 36%) as a colorless oil.

Fuente