Toluene → 6-[4-(9,10-Diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan

HRID 1912166노트

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HRID 1912166 반응식
BrC1C=CC([C:8]2[CH:21]=[CH:20][C:19]3[C:10](=[C:11]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:12]4[C:17]([C:18]=3[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:9]=2)=CC=1.[CH:34]1[C:50]2[C:42]3[C:43]4[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=4OC=3C(B(O)O)=[CH:39][C:38]=2[CH:37]=[CH:36][CH:35]=1.[C:54]1([CH3:60])[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.[C:61](=[O:64])([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:28]1([C:11]2[C:23]3[C:22]([C:18]([C:17]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)=[C:19]4[C:10]=2[CH:9]=[C:8]([C:57]2[CH:58]=[CH:59][C:54]([C:60]5[C:61]6[O:64][C:44]7[CH:46]=[CH:47][CH:48]=[CH:49][C:43]=7[C:42]=6[C:50]6[CH:34]=[CH:35][CH:36]=[CH:37][C:38]=6[CH:39]=5)=[CH:55][CH:56]=2)[CH:21]=[CH:20]4)=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 575364702-(4-Bromophenyl)-9,10-diphenylanthraceneHCID 67980539Naphtho[2,1-b]benzofuran-6-ylboronic acid

생성물 1

HCID 885401456-[4-(9,10-Diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan수율 62%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매

실험 절차

Into a 50 mL three-neck flask were placed 1.8 g (3.8 mmol) of 2-(4-bromophenyl)-9,10-diphenylanthracene and 1.0 g (3.8 mmol) of benzo[b]naphtho[1,2-d]furan-6-boronic acid synthesized in Step 1 of Example 1, 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. While the pressure was reduced, this mixture was stirred to be degassed. To this mixture was added 0.22 g (0.19 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 80° C. for 3 hours under a nitrogen stream, so that a solid was precipitated. After the mixture was cooled to room temperature, the precipitated solid was collected by suction filtration. The collected solid was purified by silica gel column chromatography (a developing solvent in which the ratio of hexane to toluene was 5:1) to give a solid. The obtained solid was recrystallized from toluene/hexane, so that 1.4 g of a yellow powder of the object of the synthesis was obtained in 62% yield.

후처리

  1. customInto a 50 mL three-neck flask were placed
  2. customto be degassed
  3. stirringthe mixture was stirred at 80° C. for 3 hours under a nitrogen stream
  4. customso that a solid was precipitated
  5. filtrationthe precipitated solid was collected by suction filtration
  6. customThe collected solid was purified by silica gel column chromatography (a developing solvent in which the ratio of hexane to toluene
  7. customto give a solid
  8. customThe obtained solid was recrystallized from toluene/hexane, so that 1.4 g of a yellow powder of the object of the synthesis
  9. customwas obtained in 62% yield

출처 및 근거

ORD 기록
ord-f2f8d78b662446d3bf55ee6907a835ee
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604224B2

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