1,2-Dibromoethane → 1H-Indene, 3,3'-(1,2-ethanediyl)bis[4,7-dimethyl-

HRID 865317

반응식

HRID 865317 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH:4]=[CH:5][CH2:6]2.[CH2:12]([Li])[CH2:13][CH2:14][CH3:15].C[C:18]1[CH:26]=[CH:25][C:24](C)=[C:23]2[C:19]=1[CH:20]=[CH:21][CH:22]2[Li].BrCCBr>O1CCCC1.O>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[C:4]([CH2:15][CH2:14][C:13]1[C:12]3[C:20](=[C:19]([CH3:23])[CH:18]=[CH:26][C:25]=3[CH3:24])[CH2:21][CH:22]=1)=[CH:5][CH2:6]2

참가 물질

7

반응물 4

HCID 78391,2-DibromoethaneHCID 814584,7-dimethyl-1H-indeneHCID 178418339ButyllithiumHCID 178506817HCID 178506817, 화합물

생성물 1

HCID 108599901H-Indene, 3,3'-(1,2-ethanediyl)bis[4,7-dimethyl-수율 48%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

38.2 g (265 mmol) of 4,7-dimethylindene was dissolved in 350 ml of tetrahydrofuran and the solution was cooled to 0° C. Then 165 ml of n-butyllithium (1,6M in hexane, 264 mmol) was added dropwise over 2.5 hours. After warming to room temperature and stirring for 4 hours a purple solution of 4,7-dimethylindenyl-lithium was obtained. This solution was cooled to -70° C. and treated dropwise with 25,3 g of 1,2-dibromoethane (135 mmol) in 15 ml of tetrahydrofuran over 35 min. After warming to room temperature, a pale yellow solution was obtained, and then water was added. The organic phase was collected and dried over Na2SO4. The solvent was removed by vacuum evaporation to provide 20 g of crude product (48% yield).

후처리

  1. temperatureAfter warming to room temperature
  2. customwas obtained
  3. temperatureThis solution was cooled to -70° C.
  4. temperatureAfter warming to room temperature
  5. customa pale yellow solution was obtained
  6. customThe organic phase was collected
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed by vacuum evaporation

출처 및 근거

ORD 기록
ord-d661a9859bd947ce97004226853d618c
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05565533

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