Potassium Phosphate, Tribasic → 3,3'-Bicarbazole

HRID 1957901노트

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HRID 1957901 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C1([N:21]2[C:33]3[CH:32]=[CH:31][C:30](B4OC(C)(C)C(C)(C)O4)=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[CH:4]1[C:5]2[NH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]=2[CH:14]=[C:2]([C:25]2[CH:24]=[CH:23][C:22]3[NH:21][C:33]4[C:28]([C:27]=3[CH:26]=2)=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:3]=1

참가 물질

8

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 2524463-BromocarbazoleHCID 574156959-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole

생성물 1

HCID 124626013,3'-Bicarbazole수율 73.1%

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

A mixture solution of 3-bromo-9H-carbazole (6.75 g, 27.4 mmol), 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (12.15 g, 32.9 mmol), Pd2(dba)3 (0.251 g, 0.274 mmol), SPhos (0.450 g, 1.097 mmol) and K3PO4 (25.3 g, 110 mmol) in toluene (500 mL) and water (50 mL) was refluxed under nitrogen for 10 h. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and washed with brine. The combined organic solutions were dried over Na2SO4, filtered, and the solvent was evaporated to yield a crude product, which was recrystallized from DCM/hexane (1/1, v/v, 1200 mL) to yield 9H,9′H-3,3′-bicarbazole (6.66 g, 59%) as a yellow solid.

후처리

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. washwashed with brine
  3. dry with materialThe combined organic solutions were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customto yield a crude product, which
  7. customwas recrystallized from DCM/hexane (1/1, v/v, 1200 mL)

출처 및 근거

ORD 기록
ord-c7513b90ab5c4dafa0b5b61a4b7432b3
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08409729B2

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