تفاعل #43934

معادلة التفاعل

3,5-diethylphenol

tetrabutylammonium tribromide

→

title compound

المردود 13.0%

4-bromo-3,5-diethylphenol

المردود 13.0%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was evaporated under reduced pressure, water
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   استخلاصthe mixture was extracted with ethyl acetate
4. 4
   غسيلThe extract was washed with saturated brine
5. 5
   تجفيفdried over anhydrous magnesium sulfate
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75)
8. 8
   أخرىthe obtained crystals were recrystallized from heptane

الإجراء التجريبي

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%).

المصدر