4,4'-Dibromobenzophenone → HCID 58085476、化合物

HRID 923703

反応式

HRID 923703 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2.C([Li])CCC.[Br:26][C:27]1[CH:41]=[CH:40][C:30]([C:31]([C:33]2[CH:38]=[CH:37][C:36]([Br:39])=[CH:35][CH:34]=2)=O)=[CH:29][CH:28]=1>O1CCCC1.C(O)(=O)C.S(=O)(=O)(O)O>[Br:26][C:27]1[CH:41]=[CH:40][C:30]([C:31]2([C:33]3[CH:38]=[CH:37][C:36]([Br:39])=[CH:35][CH:34]=3)[C:19]3[C:20]4=[C:15]([C:14]5[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=5[N:8]4[C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]2=4)[CH:16]=[CH:17][CH:18]=3)=[CH:29][CH:28]=1

参加物

7

反応物 3

HCID 728684,4'-DibromobenzophenoneHCID 594650129-(2-Bromophenyl)-9H-carbazoleHCID 178418339Butyllithium

生成物 1

HCID 58085476HCID 58085476、化合物

試薬・触媒・溶媒 3

HCID 1118Sulfuric Acid触媒HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

6.96 g of 9-(2-bromophenyl)-9H-carbazole as the intermediate of Preparation Example 8 was dissolved in 10 mL of purified tetrahydrofuran, and the resulting solution was cooled to −78° C. and 8.64 mL of butyllithium was slowly added dropwise. The mixture was stirred at the same temperature for 30 min, and 6.12 g of 4,4′-dibromobenzophenone was added. The mixture was stirred at the same temperature for 40 min and then further stirred at room temperature for an additional 3 hours. The reaction was terminated with aqueous ammonium chloride, and the reaction mixture was extracted with ethyl ether. The organic layer was dewatered using anhydrous magnesium sulfate, and the organic solvent was then removed. The resulting solid was dispersed in ethanol, stirred for one day, filtered, and vacuum dried, thus obtaining an intermediate material. The solid thus obtained was dispersed in 10 mL of acetic acid, and 10 drops of concentrated sulfuric acid were added, after which the mixture was refluxed for 4 hours. The resulting solid was filtered, washed with ethanol, and vacuum dried, yielding a 8,8-bis(4-bromophenyl)-8H-indolo[3,2,1-de]acridine compound.

後処理

  1. stirringThe mixture was stirred at the same temperature for 40 min
  2. stirringfurther stirred at room temperature for an additional 3 hours
  3. customThe reaction was terminated with aqueous ammonium chloride
  4. extractionthe reaction mixture was extracted with ethyl ether
  5. customthe organic solvent was then removed
  6. additionThe resulting solid was dispersed in ethanol
  7. stirringstirred for one day
  8. filtrationfiltered
  9. customvacuum dried
  10. customthus obtaining an intermediate material
  11. customThe solid thus obtained
  12. temperatureafter which the mixture was refluxed for 4 hours
  13. filtrationThe resulting solid was filtered
  14. washwashed with ethanol, and vacuum
  15. customdried

出典と根拠

ORDレコード
ord-abab07763426470c85969a09c21cd31b
出典データセット
uspto-grants-2016_03
特許番号
US09278986B2

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