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

HRID 1912167Notes

Reaction equation

HRID 1912167 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:14](C(C4C=CC=CC=4)=[C:16]4[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]4)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][CH:3]=1.[CH:28]1[C:44]2[C:36]3[C:37]4[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=4[O:39][C:35]=3[C:34](B(O)O)=[CH:33][C:32]=2[CH:31]=[CH:30][CH:29]=1.[C:48]1([CH3:54])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=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:48]1([C:54]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:8]([C:9]3[CH:14]=[CH:13][C:12]([C:34]4[C:35]5[O:39][C:38]6[CH:40]=[CH:41][CH:42]=[CH:43][C:37]=6[C:36]=5[C:44]5[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=5[CH:33]=4)=[CH:11][CH:10]=3)=[C:5]3[C:6]=2[CH:7]=[CH:2][CH:3]=[CH:4]3)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 221382759-(4-Bromophenyl)-10-phenylanthraceneHCID 67980539Naphtho[2,1-b]benzofuran-6-ylboronic acid

Product 1

HCID 866673116-[4-(10-Phenyl-9-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furanYield 31%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

Into a 100 mL three-neck flask were placed 1.8 g (4.5 mmol) of 9-(4-bromophenyl)-10-phenylanthracene and 1.2 g (4.5 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, 7.0 mL of ethanol, and 5.0 mL of an aqueous solution of sodium carbonate (2.0 mol/L). While the pressure was reduced, this mixture was stirred to be degassed. To this mixture was added 0.26 g (0.22 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 80° C. for 6 hours under a nitrogen stream, so that a solid was precipitated. This flask was cooled to room temperature, and this mixture was suction-filtered. The obtained solid was dissolved in about 500 mL of hot toluene, and this solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, silica gel, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). A solid obtained by concentration of the obtained filtrate was recrystallized from toluene, so that 0.77 g of a white powder of the object of the synthesis was obtained in 31% yield.

Workup

  1. customInto a 100 mL three-neck flask were placed
  2. customto be degassed
  3. stirringthe mixture was stirred at 80° C. for 6 hours under a nitrogen stream
  4. customso that a solid was precipitated
  5. filtrationthis mixture was suction-filtered
  6. dissolutionThe obtained solid was dissolved in about 500 mL of hot toluene
  7. filtrationthis solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, silica gel, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135)
  8. customA solid obtained by concentration of the obtained filtrate
  9. customwas recrystallized from toluene, so that 0.77 g of a white powder of the object of the synthesis
  10. customwas obtained in 31% yield

Sources & evidence

ORD record
ord-b5fc3ff840674c67a7009d37fbf3b64f
Source dataset
uspto-grants-2013_12
Patent number
US08604224B2

Reaction notes

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