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Sodium Carbonate → 2-[3-(9,10-Diphenyl-2-anthryl)phenyl]dibenzofuran

HRID 719044
Notes
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Reaction equation

HRID 719044 reaction equation
Br[C:2]1[CH:3]=[C:4]([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)[CH:5]=[CH:6][CH:7]=1.[CH:34]1[C:42]2[C:41]3[CH:43]=[CH:44][CH:45]=[CH:46][C:40]=3[O:39][C:38]=2[CH:37]=[CH:36][C:35]=1B(O)O.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1.CCCCCC.C(O)C>[C:28]1([C:11]2[C:12]3[C:17]([C:18]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[C:19]4[C:10]=2[CH:9]=[C:8]([C:4]2[CH:5]=[C:6]([C:35]5[CH:36]=[CH:37][C:38]6[O:39][C:40]7[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=7[C:42]=6[CH:34]=5)[CH:7]=[CH:2][CH:3]=2)[CH:21]=[CH:20]4)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 80271Tri-o-tolylphosphineHCID 12032376Dibenzo(b,d)furan-2-ylboronic Acid (contains varying amounts of Anhydride)HCID 575364512-(3-Bromophenyl)-9,10-diphenylanthracene

Product 1

HCID 582618792-[3-(9,10-Diphenyl-2-anthryl)phenyl]dibenzofuranYield 29.1%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Procedure

In a 50 mL three-neck flask were put 1.2 g (2.4 mmol) of 2-(3-bromophenyl)-9,10-diphenylanthracene, 0.52 g (2.4 mmol) of dibenzofuran-2-boronic acid, and 0.18 g (0.60 mmol) of tri(ortho-tolyl)phosphine. The air in the flask was replaced with nitrogen. To this mixture were added 10 mL of toluene, 3.0 mL of ethanol, and 3.0 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 27 mg (0.12 mmol) of palladium(II) acetate, and the mixture was stirred at 80° C. for 3 hours. Then, the aqueous layer of the obtained mixture was extracted with toluene, and the toluene solution and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate. Then, this mixture was gravity filtered. The resulting filtrate was concentrated, and the obtained oily substance was purified by silica gel column chromatography to give a yellow oily substance. The chromatography was carried out using a mixed solvent having a 5:1 ratio of hexane to toluene as a developing solvent, whereby an oily substance was obtained. Recrystallization of the oily substance from a mixed solvent of toluene and hexane gave 0.40 g of a yellow powder in 29% yield, which was the substance to be produced.

Workup

  1. customIn a 50 mL three-neck flask were put
  2. customto be degassed
  3. stirringthe mixture was stirred at 80° C. for 3 hours
  4. extractionThen, the aqueous layer of the obtained mixture was extracted with toluene
  5. washwashed with saturated brine
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe resulting filtrate was concentrated
  9. customthe obtained oily substance was purified by silica gel column chromatography
  10. customto give a yellow oily substance
  11. customwas obtained
  12. customRecrystallization of the oily substance from a mixed solvent of toluene and hexane

Sources & evidence

ORD record
ord-1533aad2830e43b6ac0917260db3e9fb
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09196836B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes