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Potassium Carbonate → 9-[4-(9,10-Diphenyl-2-anthryl)phenyl]-9H-carbazole

HRID 1774097
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인쇄 미리보기

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HRID 1774097 반응식
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:22]3C=CC=[CH:24][CH:23]=3)[C:6]3[C:11]([C:12]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[CH:28]1[C:40]2[N:39]([C:41]3[CH:46]=[CH:45][C:44](B(O)O)=[CH:43][CH:42]=3)[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]=2[CH:31]=[CH:30][CH:29]=1.[C:50]1(C)[CH:55]=CC=C[C:51]=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+].C1(C)C=CC=CC=1.C(O)C>[C:16]1([C:12]2[C:11]3[C:6]([C:5]([C:22]4[CH:23]=[CH:24][CH:55]=[CH:50][CH:51]=4)=[C:4]4[C:13]=2[CH:14]=[C:15]([C:30]2[CH:31]=[CH:32][C:40]([N:39]5[C:38]6[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=6[C:42]6[C:41]5=[CH:46][CH:45]=[CH:44][CH:43]=6)=[CH:28][CH:29]=2)[CH:2]=[CH:3]4)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 222471632-Bromo-9,10-diphenylanthraceneHCID 231208274-(9H-Carbazol-9-yl)phenylboronic Acid

생성물 1

HCID 579231609-[4-(9,10-Diphenyl-2-anthryl)phenyl]-9H-carbazole수율 54%

시약·촉매·용매 3

HCID 178476740
HCID 178476740, 화합물
촉매
HCID 702Ethanol용매
HCID 1140Toluene용매2회

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온도
100 °C

실험 절차

In a 100 mL three neck flask were put 2.0 g (4.9 mmol) of 2-bromo-9,10-diphenylanthracene, 1.4 g (4.9 mmol) of 4-(9H-carbazol-9-yl)phenylboronic acid, and 0.15 g (0.50 mmol) of tri(ortho-tolyl)phosphine, and the atmosphere in the flask was replaced with nitrogen. To this mixture were added 15 mL of toluene, 15 mL of ethanol, and 10 mL of an aqueous potassium carbonate solution (2.0 mol/L). This mixture was deaerated while being stirred under reduced pressure. Then, the atmosphere in the flask was replaced with nitrogen. To this mixture was added 23 mg (0.10 mmol) of palladium(1) acetate. This mixture was refluxed at 100° C. for 20 hours. Then, after this mixture was cooled to room temperature, about 50 mL of toluene was added thereto, and the mixture was filtered through a filter paper. The obtained mixture was washed with water, and the aqueous layer was extracted with toluene. The extract solution and the organic layer were combined and washed with a saturated saline solution, and the organic layer was dried with magnesium sulfate. This mixture was gravity filtered. The obtained filtrate was concentrated to give a light yellow solid. This solid was washed with toluene to give the object of the synthesis as 1.5 g of a light yellow powdered solid in a yield of 54%.

후처리

  1. temperatureThen, after this mixture was cooled to room temperature
  2. filtrationthe mixture was filtered through a filter paper
  3. washThe obtained mixture was washed with water
  4. extractionthe aqueous layer was extracted with toluene
  5. washwashed with a saturated saline solution
  6. dry with materialthe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe obtained filtrate was concentrated
  9. customto give a light yellow solid
  10. washThis solid was washed with toluene
  11. customto give

출처 및 근거

ORD 기록
ord-79f3ef8ac6a54f7bb9fd7d7bb8337bd6
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09257654B2

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