Ethanol → 9-(Naphthalen-1-yl)-10-(7-phenylnaphthalen-2-yl)anthracene

HRID 2179849Notes

Reaction equation

HRID 2179849 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([C:17]3[C:18]4[C:23]([C:24](C5C6C(=CC=CC=6)C=CC=5)=[C:25]5[C:30]=3[CH:29]=[CH:28][CH:27]=[CH:26]5)=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:12][CH:13]=2)[CH:8]=1)(=O)=O.[C:43]1(B(O)O)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:60](O)[CH3:61]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.CO.O>[C:43]1([C:24]2[C:23]3[C:18]([C:17]([C:11]4[CH:12]=[CH:13][C:14]5[C:9](=[CH:8][C:7]([C:61]6[CH:60]=[CH:13][CH:12]=[CH:11][CH:10]=6)=[CH:16][CH:15]=5)[CH:10]=4)=[C:30]4[C:25]=2[CH:26]=[CH:27][CH:28]=[CH:29]4)=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:48]2[C:47](=[CH:16][CH:7]=[CH:8][CH:9]=2)[CH:46]=[CH:45][CH:44]=1

Participants

10

Reactant 4

HCID 702EthanolHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 867013487-(10-(Naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl trifluoromethane sulfonate

Product 1

HCID 867013499-(Naphthalen-1-yl)-10-(7-phenylnaphthalen-2-yl)anthracene

Reagents, catalysts & solvents 5

HCID 75806TricyclohexylphosphineCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

Under the nitrogen atmosphere, (7-(10-(naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl trifluoromethane sulfonate (3.0 g) as the fifth intermediate compound, phenylboronic acid (0.8 g), bis(dibenzylideneacetone)palladium (0) (Pd(dba)2) (0.03 g), tricyclohexyl phosphine (PCy3) (0.03 g), potassium phosphate (2.2 g), and a mixture solvent (22 ml) of toluene, ethanol, and water (toluene/ethanol/water=9/1/1 (volume ratio)) were added to a flask and refluxed for 2.5 hours. Once the heating is completed, the reaction solution was cooled to room temperature and added with methanol. The precipitates were collected by suction filtration. The obtained solid was washed with water followed by methanol, and washed further with ethyl acetate. The obtained crude product was dissolved in toluene, and colored components were removed by passing through an active carbon short column. After re-crystallization with chlorobenzene, 9-(naphthalen-1-yl)-10-(7-phenylnaphthalen-2-yl)anthracene (1.2 g) was obtained as the target compound represented by Formula (1-1). The scheme is shown in the following “Reaction 7”.

Workup

  1. temperaturerefluxed for 2.5 hours
  2. filtrationThe precipitates were collected by suction filtration
  3. washThe obtained solid was washed with water
  4. washwashed further with ethyl acetate
  5. customThe obtained crude product
  6. customcolored components were removed
  7. customAfter re-crystallization with chlorobenzene

Sources & evidence

ORD record
ord-56031cb56adf4e81b66864a019be5b44
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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