Ethanol → Anthracene

HRID 2179851Notes

Reaction equation

HRID 2179851 reaction equation
FC(F)(F)S(OC1C=CC2C(=CC([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)=CC=2)C=1)(=O)=O.C1(C2C=CC(B(O)O)=CC=2)C2C(=CC=CC=2)C=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)C>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>[CH:19]1[C:18]2[C:23](=[CH:24][C:25]3[C:30]([CH:17]=2)=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:22]=[CH:21][CH:20]=1

Participants

10

Reactant 4

HCID 702EthanolHCID 62657Potassium Phosphate, TribasicHCID 441193994-(1-Naphthyl)phenylboronic Acid (contains varying amounts of Anhydride)HCID 867013487-(10-(Naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl trifluoromethane sulfonate

Product 1

HCID 8418AnthraceneYield 281.4%

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, (4-(naphthalen-1-yl)phenyl)boronic acid (1.9 g), bis(dibenzylideneacetone)palladium (0) (Pd(dba)2) (0.03 g), tricyclohexyl phosphine (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 6.5 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 a silica gel short column. The solvent was distilled off under reduced pressure. The obtained oily phase substance was added with ethyl acetate and the precipitated products were collected by suction filtration to give 9-(naphthalen-1-yl)-10-(7-(naphthalen-1-yl)phenyl)naphthalen-2-yl)anthracene (2.6 g) as the target compound represented by Formula (1-21). The scheme is illustrated in the following “Reaction 9”.

Workup

  1. temperaturerefluxed for 6.5 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. distillationThe solvent was distilled off under reduced pressure
  8. additionThe obtained oily phase substance was added with ethyl acetate
  9. filtrationthe precipitated products were collected by suction filtration

Sources & evidence

ORD record
ord-b115ea772ac14afda87a157490d25ca9
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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