2-Bromobenzoyl chloride → (2-bromophenyl)-(3,8-diphenyl-12H-11,12-diazaindeno[2,1-a]fluoren-11-yl)methanone

HRID 76381

반응식

HRID 76381 반응식
[H-].[Na+].[CH:3](=[C:5](/[C:10]1[CH:35]=[C:34]2[C:13]([NH:14][C:15]3[C:16]2=[CH:17][CH:18]=[C:19]2[C:27]=3[NH:26][C:25]3[C:20]2=[CH:21][C:22]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:23][CH:24]=3)=[CH:12][CH:11]=1)\[CH:6]=[CH:7]/[CH:8]=C)\[CH3:4].C1OCCOCCOCCOCCOC1.[Br:51][C:52]1[CH:60]=[CH:59][CH:58]=[CH:57][C:53]=1[C:54](Cl)=[O:55]>C1COCC1>[Br:51][C:52]1[CH:60]=[CH:59][CH:58]=[CH:57][C:53]=1[C:54]([N:26]1[C:27]2[C:19](=[CH:18][CH:17]=[C:16]3[C:34]4[C:13](=[CH:12][CH:11]=[C:10]([C:5]5[CH:6]=[CH:7][CH:8]=[CH:4][CH:3]=5)[CH:35]=4)[NH:14][C:15]3=2)[C:20]2[C:25]1=[CH:24][CH:23]=[C:22]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:21]=2)=[O:55]

참가 물질

6

반응물 4

HCID 235422-Bromobenzoyl chlorideHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 873866343-[(Z)-1-eth-(E)-ylidenepenta-2,4-dienyl]-8-phenyl-11,12-dihydro-11,12-diazaindeno[2,1-a]-fluorene

생성물 1

HCID 67428432(2-bromophenyl)-(3,8-diphenyl-12H-11,12-diazaindeno[2,1-a]fluoren-11-yl)methanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

2.1 g (52.5 mmol) of NaH (60% in mineral oil) are dissolved in 500 ml of THF under a protective atmosphere. 20 g (50 mmol) of 3-[(Z)-1-eth-(E)-ylidenepenta-2,4-dienyl]-8-phenyl-11,12-dihydro-11,12-diazaindeno[2,1-a]-fluorene and 11.5 g (52.5 mmol) of 15-crown-5 dissolved in 200 ml of THF are added. After 1 h at room temperature, a solution of 12 g (55 mmol) of 2-bromobenzoyl chloride in 250 ml of THF is added dropwise. The reaction mixture is stirred at room temperature for 18 h. After this time, the reaction mixture is poured onto ice and extracted three times with dichloromethane. The combined organic phases are dried over Na2SO4 and evaporated. The residue is extracted with hot toluene and recrystallised from toluene/n-heptane. The yield is 22 g (75%).

후처리

  1. additionare added
  2. additionAfter this time, the reaction mixture is poured onto ice
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated
  6. extractionThe residue is extracted with hot toluene
  7. customrecrystallised from toluene/n-heptane

출처 및 근거

ORD 기록
ord-8528ae3921104bff8e5c266bb76f097b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835626B2

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