Reacción #43934

Ecuación de reacción

3,5-diethylphenol

tetrabutylammonium tribromide

→

title compound

Rendimiento 13.0%

4-bromo-3,5-diethylphenol

Rendimiento 13.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was evaporated under reduced pressure, water
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   Extracciónthe mixture was extracted with ethyl acetate
4. 4
   LavadoThe extract was washed with 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=0:100-25:75)
8. 8
   Otrothe obtained crystals were recrystallized from heptane

Procedimiento

To a solution of 3,5-diethylphenol (9.30 g, 61.9 mmol) in methanol (100 mL) was added tetrabutylammonium tribromide (29.8 g, 61.9 mmol), and the mixture was stirred at room temperature for 15 hr. The solvent was evaporated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75), and the obtained crystals were recrystallized from heptane to give the title compound (1.85 g) as colorless crystals. The mother liquor was concentrated under reduced pressure to give the title compound (8.68 g) as dark-brown crystals (total 10.5 g, total yield 74%).

Fuente