Toluene → 7-[4-(10-Phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole

HRID 876189노트

반응식

HRID 876189 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:20]3[CH:19]=[CH:18][C:17]4[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=4[C:15]=3[C:14]3[C:13]4[CH:25]=[CH:26][CH:27]=[CH:28][C:12]=4[CH:11]=[CH:10][C:9]2=3)=[CH:4][CH:3]=1.[C:29]1([C:35]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:42](B(O)O)=[C:41]3[C:36]=2[CH:37]=[CH:38][CH:39]=[CH:40]3)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C(O)C>[C:29]1([C:35]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:42]([C:2]3[CH:7]=[CH:6][C:5]([N:8]4[C:9]5[CH:10]=[CH:11][C:12]6[CH:28]=[CH:27][CH:26]=[CH:25][C:13]=6[C:14]=5[C:15]5[C:16]6[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=6[CH:18]=[CH:19][C:20]4=5)=[CH:4][CH:3]=3)=[C:41]3[C:36]=2[CH:37]=[CH:38][CH:39]=[CH:40]3)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 22247164(10-Phenylanthracen-9-yl)boronic acidHCID 712238227-(4-Bromophenyl)-7H-dibenzo[c,g]carbazole

생성물 1

HCID 866758387-[4-(10-Phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole수율 55%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매

실험 절차

In a 200 mL three-neck flask were placed 1.7 g (4.0 mmol) of 7-(4-bromophenyl)-7H-dibenzo[c,g]carbazole and 1.2 g (4.0 mmol) of 10-phenylanthracene-9-boronic acid, and the air in the flask was replaced with nitrogen. To this mixture were added 15 mL of toluene, 5.0 mL of ethanol, and 4.0 mL of an aqueous solution of sodium carbonate. This mixture was degassed by being stirred while the pressure was reduced. To this mixture was added 0.23 g (0.20 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 90° C. for 10 hours under a nitrogen stream, so that a solid was precipitated. The precipitated solid was removed by suction filtration. The collected solid was dissolved in about 50 mL of hot toluene, and this solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). A solid obtained by concentration of the filtrate was washed with toluene/hexane to give 1.3 g of a pale yellow powder, which was the object of the synthesis, in a yield of 55%. A synthesis scheme (d-2) of Step 4 is illustrated below.

후처리

  1. customIn a 200 mL three-neck flask were placed
  2. customThis mixture was degassed
  3. stirringthe mixture was stirred at 90° C. for 10 hours under a nitrogen stream
  4. customso that a solid was precipitated
  5. customThe precipitated solid was removed by suction filtration
  6. dissolutionThe collected solid was dissolved in about 50 mL of hot toluene
  7. filtrationthis solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135)
  8. customA solid obtained by concentration of the filtrate
  9. washwas washed with toluene/hexane

출처 및 근거

ORD 기록
ord-1286cadd3e0743a680245c98aa667ccf
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08986857B2

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