1,2-Dimethoxyethane → 3,6-DI-Tert-butyl-2,7-diphenyl-9H-fluorene

HRID 909116노트

반응식

HRID 909116 반응식
Br[C:2]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[C:9]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.CO[CH2:26][CH2:27]OC.[C:30]1(OB(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:30]1([C:2]2[C:14]([C:15]([CH3:17])([CH3:18])[CH3:16])=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][C:8]([C:27]5[CH:26]=[CH:4][CH:3]=[CH:2][CH:14]=5)=[C:9]([C:19]([CH3:20])([CH3:22])[CH3:21])[CH:10]=4)[CH2:5][C:4]=3[CH:3]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

6

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 135475422,7-Dibromo-3,6-DI-tert-butyl-9H-fluorene

생성물 1

HCID 219826953,6-DI-Tert-butyl-2,7-diphenyl-9H-fluorene수율 54%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

In a nitrogen atmosphere, 8.15 g (18.7 mmol) of 2,7-dibromo-3,6-di-tert-butyl-fluorene and 1.08 g (0.93 mmol) of Pd(PPh3) were added to a 300 mL three-neck flask, and then 120 mL of dehydrated 1,2-dimethoxyethane was added and the mixture was stirred at room temperature for 20 min. To the solution obtained, 20 mL of ethanol solution containing 5.01 g (41.1 mmol) of phenyl boric acid was added and the mixture was stirred at room temperature for 20 min, and then 37.4 mL (74.8 mmol) of a 2.0 mol/L sodium carbonate aqueous solution was added. Thereafter, the mixture was refluxed while heating for 18 hr and cooled spontaneously, and then quenched with dilute hydrochloric acid in an ice bath. The soluble part was extracted by adding ether, and the organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution twice, with water twice and with saturated brine twice, and then dried with magnesium sulfate. Thereafter, the solvent was distilled off and the resulting solid was separated with a column chromatography to prepare an aimed product (in an amount of 4.36 g in a yield of 54%). The identification of the aimed product was carried out by 1H-NMR and FD-MS spectrum.

후처리

  1. customTo the solution obtained
  2. additionwas added
  3. stirringthe mixture was stirred at room temperature for 20 min
  4. temperatureThereafter, the mixture was refluxed
  5. temperaturewhile heating for 18 hr
  6. temperaturecooled spontaneously
  7. customquenched with dilute hydrochloric acid in an ice bath
  8. extractionThe soluble part was extracted
  9. additionby adding ether
  10. washthe organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution twice
  11. dry with materialwith water twice and with saturated brine twice, and then dried with magnesium sulfate
  12. distillationThereafter, the solvent was distilled off
  13. customthe resulting solid was separated with a column chromatography
  14. customto prepare an aimed product (in an amount of 4.36 g in a yield of 54%)

출처 및 근거

ORD 기록
ord-0354c7c9b4c94c0a81f6c42dac01e5ea
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017705B2

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