Magnesium Bromide → 2-(3,5-di-t-Butylphenyl)indene

HRID 411814

반응식

HRID 411814 반응식
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:3]=1.C([Li])(C)(C)C.[Br-].[Mg+2].[Br-].Br[C:25]1[CH2:26][C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][CH:28]=2>CCOCC>[C:12]([C:4]1[CH:3]=[C:2]([C:25]2[CH2:33][C:32]3[C:27]([CH:26]=2)=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=1)([CH3:15])([CH3:14])[CH3:13]

참가 물질

6

반응물 4

HCID 82241Magnesium BromideHCID 5755861H-Indene, 2-bromo-HCID 6201361-Bromo-3,5-di-tert-butylbenzeneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 222838282-(3,5-di-t-Butylphenyl)indene수율 70%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

1-Bromo-3,5-di-t-butylbenzene (47.2 g, 0.175 mol) was dissolved in ether (500 mL) and cooled to −70° C. t-Butyllithium (200 mL of 1.7 M solution in pentane, 0.34 mol) was added at −70° C. over a two hour period. The solution was allowed to warm to room temperature slowly. Magnesium bromide etherate (46.5 g, 0.18 mol) was added and the slurry was stirred for one hour. The mixture was then cooled to 5° C. and 2-bromoindene (34.2 g, 0.18 mol) was added. The mixture was warmed to room temperature and then refluxed for three hours. The solution was cooled to room temperature and the reaction was quenched carefully with water. The layers were separated and the organics washed with salt brine and dried over magnesium sulfate. The solvents were evaporated and the product was distilled twice and recrystallized from hexane to give 37.1 g of product (70%).

후처리

  1. additionwas added at −70° C. over a two hour period
  2. temperatureThe mixture was then cooled to 5° C.
  3. temperatureThe mixture was warmed to room temperature
  4. temperaturerefluxed for three hours
  5. temperatureThe solution was cooled to room temperature
  6. customthe reaction was quenched carefully with water
  7. customThe layers were separated
  8. washthe organics washed with salt brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvents were evaporated
  11. distillationthe product was distilled twice
  12. customrecrystallized from hexane

출처 및 근거

ORD 기록
ord-8a9116e738dd4165b9915d7404669b6a
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559262B1

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