تفاعل #1148667

معادلة التفاعل

1,3,5-Tri-t-butylbenzene

bromine

→

product

المردود 46.4%

Bromo-3,5-di-t-butylbenzene

المردود 46.4%

المذيبات

carbon tetrachloride

carbon tetrachloride

ظروف التفاعل

المعالجة

1. 1
   أخرىequipped with an overhead stirrer
2. 2
   workup.ADDITIONthermometer and addition funnel under argon
3. 3
   workup.ADDITIONwere added
4. 4
   workup.ADDITIONwas added
5. 5
   أخرىquenched
6. 6
   workup.ADDITIONby pouring into ice water
7. 7
   أخرىThe layers were separated
8. 8
   غسيلthe organics washed with 10% sodium hydroxide solution
9. 9
   غسيلThe solution was then washed with salt brine
10. 10
    تجفيفdried over magnesium sulfate
11. 11
    أخرىThe solvent was evaporated
12. 12
    workup.DISTILLATIONthe product was distilled under vacuum twice

الإجراء التجريبي

1,3,5-Tri-t-butylbenzene (150 g, 0.6 mol) was dissolved in carbon tetrachloride (300 mL) in a three-necked flask which had been painted black to avoid light and equipped with an overhead stirrer, thermometer and addition funnel under argon. Iron pellets (36 g, 0.64 mol) were added and the slurry was cooled to 5° C. t-Butylcatechol (1.0 g) was added and a solution of bromine (201.6 g, 1.26 mol) in carbon tetrachloride (75 mL) was added over a one hour period. The slurry was stirred for an additional 4 hours at 5° C. and quenched by pouring into ice water. The layers were separated and the organics washed with 10% sodium hydroxide solution. The solution was then washed with salt brine and dried over magnesium sulfate. The solvent was evaporated and the product was distilled under vacuum twice to give 75 g of product which was then recrystallized from heptane to give 47 g of pure product (29%).

المصدر