Toluene → 9-([1,1':3',1''-Terphenyl]-5'-yl)-10-([2,2'-binaphthalen]-7-yl)anthracene

HRID 2179857노트

반응식

HRID 2179857 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[C:12]4[C:17]([C:18](Br)=[C:19]5[C:24]=3[CH:23]=[CH:22][CH:21]=[CH:20]5)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=1.[C:36]1([C:42]2[CH:47]=[C:46](B(O)O)[CH:45]=[C:44]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH:43]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(O)C>[C:36]1([C:42]2[CH:47]=[C:46]([C:18]3[C:19]4[C:24]([C:11]([C:8]5[CH:9]=[C:10]6[C:5]([CH:4]=[CH:3][C:2]([C:26]7[CH:35]=[CH:34][C:33]8[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=8)[CH:27]=7)=[CH:1]6)=[CH:6][CH:7]=5)=[C:12]5[C:17]=3[CH:16]=[CH:15][CH:14]=[CH:13]5)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:45]=[C:44]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH:43]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 14739363(1~1~,2~1~:2~3~,3~1~-Terphenyl)-2~5~-ylboronic acidHCID 867013529-([2,2'-Binaphthalen]-7-yl)-10-bromoanthracene

생성물 1

HCID 867013559-([1,1':3',1''-Terphenyl]-5'-yl)-10-([2,2'-binaphthalen]-7-yl)anthracene수율 41.6%

시약·촉매·용매 3

HCID 75806Tricyclohexylphosphine촉매HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 702Ethanol용매

실험 절차

Under the nitrogen atmosphere, [9-([2,2′-binaphthalen]-7-yl)-10-bromoanthracene (2.0 g) as the tenth intermediate compound, [1,1′:3′,1″-terphenyl]-5′-ylboronic acid (1.0 g), Pd(dba)2 (0.03 g), tricyclohexyl phosphine (0.03 g), potassium phosphate (1.3 g), and a mixture solvent of toluene and ethanol (20 ml) (toluene/ethanol=4/1 (volume ratio)) were added to a flask and refluxed for 2 hours. Once the heating is completed, the reaction solution was cooled to room temperature. The reaction was terminated by adding water. The target compound was extracted with toluene. The solvent was distilled off under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (solvent: toluene) and also by active carbon column chromatography (solvent: toluene) to give 9-([1,1′:3′,1″-terphenyl]-5′-yl)-10-([2,2′-binaphthalen]-7-yl)anthracene (1.0 g) as the target compound represented by Formula (1-162). The scheme is shown in the following “Reaction 17”.

후처리

  1. temperaturerefluxed for 2 hours
  2. customThe reaction was terminated
  3. additionby adding water
  4. extractionThe target compound was extracted with toluene
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained crude product
  7. customwas purified by silica gel column chromatography (solvent: toluene) and also by active carbon column chromatography (solvent: toluene)

출처 및 근거

ORD 기록
ord-6158255d007747f1a36dd87fc4b56f0b
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09070885B2

반응 노트

불러오는 중…