Triethylamine → 9,10-Diphenylanthracene

HRID 1244976

Reaction equation

HRID 1244976 reaction equation
C(N([CH2:6][CH3:7])CC)C.Cl[C:9]1[C:10]2[C:15]([C:16](Cl)=[C:17]3[C:22]=1[CH:21]=[CH:20][CH:19]=[CH:18]3)=[CH:14][CH:13]=[CH:12][CH:11]=2.C[Mg]Br.[C:27]1([Mg]Br)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1.Cl[Ni]Cl.C1(C)C=CC=CC=1>[C:27]1([C:9]2[C:10]3[C:15]([C:16]([C:7]4[CH:6]=[CH:21][CH:22]=[CH:9][CH:10]=4)=[C:17]4[C:22]=2[CH:21]=[CH:20][CH:19]=[CH:18]4)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 118009,10-DichloroanthraceneHCID 178418255HCID 178418255, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 151599,10-DiphenylanthraceneYield 80.4%

Reagents, catalysts & solvents 3

HCID 24385Nickel DichlorideCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, 194.4 mg (1.5 mmol) of dry NiCl2 and 303 mg (3 mmol) of triethylamine were added to 29.99 g of toluene and were stirred at room temperature for 10 minutes. Subsequently, 7.41 g (30.0 mol) of 9,10-dichloroanthracene was added at that temperature and reduced-pressure nitrogen replacement was conducted. To the reaction mixture, 3.8 ml (3.8 mmol) of a 1.0 mol/l solution of methylmagnesium bromide in tetrahydrofuran was added and then stirred at 25° C. for another 10 minutes. To the resulting reaction mixture, 69 ml (69 mmol) of a 1 mol/l solution of phenylmagnesium bromide in tetrahydrofuran was added dropwise over 50 minutes and stirred for 4 hours while being heated under reflux. The resulting mixture was washed once with 54.7 g of a saturated aqueous ammonium chloride solution and twice with 50.4 g of ion exchange water. To the organic layer, 50.4 g of methanol was added dropwise and then cooled to room temperature. Crystals formed were separated by filtration, washed with 30.4 g of in ethanol and dried, resulting in 7.97 g of desired 9,10-diphenylanthracene (yield: 80.4%, purity: 99% or higher). No triethylamine was detected in the crystals. The filtrate contained 12%, in terms of yield, of 9,10-diphenylanthracene.

Workup

  1. stirringstirred at 25° C. for another 10 minutes
  2. additionwas added dropwise over 50 minutes
  3. stirringstirred for 4 hours
  4. temperaturewhile being heated
  5. temperatureunder reflux
  6. washThe resulting mixture was washed once with 54.7 g of a saturated aqueous ammonium chloride solution and twice with 50.4 g of ion exchange water
  7. additionTo the organic layer, 50.4 g of methanol was added dropwise
  8. temperaturecooled to room temperature
  9. customCrystals formed
  10. customwere separated by filtration
  11. washwashed with 30.4 g of in ethanol
  12. customdried

Sources & evidence

ORD record
ord-b31aef6bcada43e1af6984943cd7aa33
Source dataset
uspto-grants-2006_10
Patent number
US07122711B2

Linked notes

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