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Toluene → 4-(2-Triphenylenyl)dibenzothiophene

HRID 1748949
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HRID 1748949 반응식
Br[C:2]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1.[CH:20]1[C:28]2[C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[S:25][C:24]=2[C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH:3]1[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]=2[CH:18]=[CH:19][C:2]=1[C:32]1[C:26]2[S:25][C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:28]=3[C:27]=2[CH:29]=[CH:30][CH:31]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 2734329Dibenzothiophene-4-boronic acidHCID 183811742-Bromotriphenylene

생성물 1

HCID 594892474-(2-Triphenylenyl)dibenzothiophene수율 86%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매

실험 절차

4.4 g (14.6 mmol) of 2-bromotriphenylene, 4.0 g (17.5 mmol) of 4-dibenzothiopheneboronic acid, 0.51 g (0.44 mmol) of tetrakistriphenylphosphinepalladium, and 4.0 g (43.4 mmol) of potassium carbonate were charged in a 250 mL round bottom flask with solvent 90 mL of toluene and 10 mL of water. The reaction mixture was purged with nitrogen for 30 min and then was heated up to reflux for overnight under nitrogen with stirring. The reaction mixture was cooled and the organic extracts were purified by column chromatography and recrystallization with toluene. 5.1 g (86%) of white solid was obtained as the product which was confirmed by proton NMR.

후처리

  1. customThe reaction mixture was purged with nitrogen for 30 min
  2. temperaturewas heated up
  3. temperatureto reflux for overnight under nitrogen
  4. temperatureThe reaction mixture was cooled
  5. customthe organic extracts were purified by column chromatography and recrystallization with toluene

출처 및 근거

ORD 기록
ord-d82432693f5348bca5b804a083f3d703
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09153786B2

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