1,1-Dibromoethane → 1,2-Bis(2-methyl-4-phenylindenyl)ethane

HRID 1004791노트

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HRID 1004791 반응식
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][C:7]1[CH2:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Br[CH:23](Br)[CH3:24]>C1(C)C=CC=CC=1.C1COCC1>[CH3:4][C:3]1[CH:21]([CH2:23][CH2:24][CH:15]2[C:14]3[C:9](=[C:10]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:11]=[CH:12][CH:13]=3)[CH:8]=[C:7]2[CH3:6])[C:20]2[C:1]([CH:2]=1)=[C:16]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:9]=1)[CH:17]=[CH:18][CH:19]=2

참가 물질

6

반응물 3

HCID 112011,1-DibromoethaneHCID 42924022-Methyl-7-phenylindeneHCID 178418339Butyllithium

생성물 1

HCID 229949181,2-Bis(2-methyl-4-phenylindenyl)ethane수율 5%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

90 cm3 (0.24 mol) of a 20% strength solution of butyllithium in toluene were added at room temperature under argon to a solution of 50 g (0.24 mol) of 3 in 500 ml of THF. The mixture was stirred at 60° C. for 2 hours, and cooled to -78° C., 22.5 g (0.12 mol) of dibromoethane were added, and the mixture was warmed to room temperature over the course of 18 hours. The reaction mixture was washed with 50 cm3 of H2O, the solvent was removed in vacuo, and the residue was chromatographed on 500 g of silica gel (hexane/methylene chloride 9:1), giving 2.5 g (5%) of 32 as a yellow oil which solidified slowly at -20° C.

후처리

  1. temperaturecooled to -78° C.
  2. temperaturethe mixture was warmed to room temperature over the course of 18 hours
  3. washThe reaction mixture was washed with 50 cm3 of H2O
  4. customthe solvent was removed in vacuo
  5. customthe residue was chromatographed on 500 g of silica gel (hexane/methylene chloride 9:1)

출처 및 근거

ORD 기록
ord-aa7b81d081ba49d49903b4fd3b58ff84
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06051727

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