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

HRID 1912166Notes

Reaction equation

HRID 1912166 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f2f8d78b662446d3bf55ee6907a835ee
Source dataset
uspto-grants-2013_12
Patent number
US08604224B2

Reaction notes

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