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

HRID 76381

反応式

HRID 76381 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-8528ae3921104bff8e5c266bb76f097b
出典データセット
uspto-grants-2014_09
特許番号
US08835626B2

関連ノート

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