1,3,5-Tri-tert-butylbenzene → 1-Bromo-3,5-di-tert-butylbenzene

HRID 1017141

반응식

HRID 1017141 반응식
[C:1]([C:5]1[CH:10]=[C:9](C(C)(C)C)[CH:8]=[C:7]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:19]Br>C(Cl)(Cl)(Cl)Cl.[Fe].C(C1C=CC=C(O)C=1O)(C)(C)C>[Br:19][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=[C:7]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:8]=1

참가 물질

6

반응물 2

HCID 150891,3,5-Tri-tert-butylbenzeneHCID 24408Bromine

생성물 1

HCID 6201361-Bromo-3,5-di-tert-butylbenzene수율 46.4%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 77643tert-Butylcatechol촉매HCID 5943Carbon Tetrachloride용매2회

반응 조건

온도
5 °C

실험 절차

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 then was 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% yield).

후처리

  1. customequipped with an overhead stirrer
  2. additionthermometer and addition funnel under argon
  3. additionwas added
  4. customquenched
  5. additionby pouring into ice water
  6. customThe layers were separated
  7. washthe organics washed with 10% sodium hydroxide solution
  8. washThe solution then was washed with salt brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was evaporated
  11. distillationthe product was distilled under vacuum twice

출처 및 근거

ORD 기록
ord-220913932a814915b0fc33d433d1ec05
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479424B1

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