Diisopentyl ether → 2,3-Diphenyl-1,1-bis(3,5-dibromophenyl)-1H-indene

HRID 2241177

반응식

HRID 2241177 반응식
Br[C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Mg].C(OCCC(C)C)CC(C)C.[Br:34][C:35]1[CH:36]=[C:37]([CH:48]=[C:49]([Br:51])[CH:50]=1)[C:38]([C:40]1[CH:45]=[C:44]([Br:46])[CH:43]=[C:42]([Br:47])[CH:41]=1)=O>CCCCCC>[C:16]1([C:2]2[C:38]([C:40]3[CH:45]=[C:44]([Br:46])[CH:43]=[C:42]([Br:47])[CH:41]=3)([C:37]3[CH:36]=[C:35]([Br:34])[CH:50]=[C:49]([Br:51])[CH:48]=3)[C:11]3[C:10]([C:3]=2[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

6

반응물 4

HCID 10989Diisopentyl etherHCID 153541-Bromo-1,2,2-triphenyletheneHCID 5462224MagnesiumHCID 11547805Methanone, bis(3,5-dibromophenyl)-

생성물 1

HCID 593065722,3-Diphenyl-1,1-bis(3,5-dibromophenyl)-1H-indene수율 79%

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

A mixture of bromotriphenylethylene (14.143 g, 42.19 mmol), magnesium (903 mg, 37.2 mmol) and i-pentylether (100 cm3) was heated to reflux for 1.75 h. Heating was temporarily removed and 1 (14.00 g, 28.12 mmol) was added. The mixture was heated to reflux under nitrogen for 20 h and then allowed to cool. Hexane (100 cm3) was added and the mixture was allowed to stand for 30 min. The resultant precipitate was collected and washed with hexane. The solid was mixed with dichloromethane (200 cm3) and aqueous ammonium chloride (1 M, 200 cm3) and stirred until fully dissolved. The aqueous layer was separated and extracted with dichloromethane (3×30 cm3) and the combined organic layers washed with aqueous ammonium chloride (1 M, 100 cm3) and water (100 cm3), dried over anhydrous magnesium sulphate, filtered and the solvent removed. The residue was triturated with boiling ethanol, cooled and filtered to give 2 (16.34 g, 79%) as a white solid.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 1.75 h
  3. temperatureHeating
  4. customwas temporarily removed
  5. temperatureThe mixture was heated
  6. temperatureto reflux under nitrogen for 20 h
  7. temperatureto cool
  8. customThe resultant precipitate was collected
  9. washwashed with hexane
  10. additionThe solid was mixed with dichloromethane (200 cm3) and aqueous ammonium chloride (1 M, 200 cm3)
  11. dissolutionuntil fully dissolved
  12. customThe aqueous layer was separated
  13. extractionextracted with dichloromethane (3×30 cm3)
  14. washthe combined organic layers washed with aqueous ammonium chloride (1 M, 100 cm3) and water (100 cm3)
  15. dry with materialdried over anhydrous magnesium sulphate
  16. filtrationfiltered
  17. customthe solvent removed
  18. customThe residue was triturated with boiling ethanol
  19. temperaturecooled
  20. filtrationfiltered

출처 및 근거

ORD 기록
ord-0671fea9223642e3a68155cca5c7fa13
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723553B2

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