Potassium Carbonate → 9-Phenylanthracene

HRID 444662

반응식

HRID 444662 반응식
Br[C:2]1[C:3]2[C:8]([CH:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COCCOC>[C:16]1([C:2]2[C:3]3[C:8]([CH:9]=[C:10]4[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 740629-BromoanthraceneHCID 80271Tri-o-tolylphosphine

생성물 1

HCID 117669-Phenylanthracene수율 85%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

Into a 200 mL three-neck flask were put 5.4 g (21 mmol) of 9-bromoanthracene, 2.6 g (21 mmol) of phenylboronic acid, 60 mg (0.2 mmol) of palladium(II) acetate (abbreviation: Pd(OAc)2), 10 mL (20 mmol) of potassium carbonate aqueous solution (2.0 mol/L), 260 mg (0.8 mmol) of tris(o-tolyl)phosphine (abbreviation: P(o-tolyl)3), and 20 mL of 1,2-dimethoxyethane (abbreviation: DME), and then the mixture was stirred at 80° C. in a nitrogen atmosphere for 9 hours. After the reaction, a precipitated solid was collected by suction filtration, dissolved in toluene, and filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina. The obtained filtrate was washed with water and saturated aqueous solution and magnesium sulfate was added so that the moisture was removed. This suspending solution was naturally filtered and the obtained filtrate was concentrated, whereby 22 g of a light-brown solid of 9-phenylanthracene, which was the object of the synthesis, was obtained in a yield of 85% (synthesis scheme (a-1)).

후처리

  1. customInto a 200 mL three-neck flask were put
  2. customAfter the reaction
  3. filtrationa precipitated solid was collected by suction filtration
  4. dissolutiondissolved in toluene
  5. filtrationfiltered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina
  6. washThe obtained filtrate was washed with water and saturated aqueous solution and magnesium sulfate
  7. additionwas added so that the moisture
  8. customwas removed
  9. filtrationThis suspending solution was naturally filtered
  10. concentrationthe obtained filtrate was concentrated
  11. customthe object of the synthesis
  12. customwas obtained in a yield of 85% (synthesis scheme (a-1))

출처 및 근거

ORD 기록
ord-bd8731d07a4b4e3abd48af477f59ad25
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08475935B2

연결된 노트

불러오는 중…