Potassium Carbonate → 9-Phenylanthracene

HRID 535234

反応式

HRID 535234 の反応式
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.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.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

参加物

8

反応物 4

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

生成物 1

HCID 117669-Phenylanthracene

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

In a 200 mL three-neck flask, 6.4 g (25 mmol) of 9-bromoanthracene, 3.0 g (25 mmol) of phenylboronic acid, 0.76 g (2.5 mmol) of tri(ortho-tolyl)phosphine, 60 mL of ethylene glycol dimethyl ether (DME), and 25 mL of a 2.0 M potassium carbonate solution were placed. The mixture was degassed by being stirred under reduced pressure, and the air in the flask was replaced with nitrogen. To the mixture, 0.11 g (0.50 mmol) of palladium(II) acetate was added and stirred under nitrogen stream at 80° C. for 3 hours. After a certain period, water was added to the mixture, and an aqueous layer was extracted with toluene. The obtained extracted solution and the organic layer were combined and washed with saturated saline, and the organic layer was dried with magnesium sulfate. The mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina, and the filtrate was condensed to give a solid. The solid was recrystallized with toluene/methonol, so that 5.8 g of target white powder was obtained in a yield of 92%.

後処理

  1. customThe mixture was degassed
  2. stirringstirred under nitrogen stream at 80° C. for 3 hours
  3. waitAfter a certain period
  4. extractionan aqueous layer was extracted with toluene
  5. extractionThe obtained extracted solution
  6. washwashed with saturated saline
  7. dry with materialthe organic layer was dried with magnesium sulfate
  8. filtrationThe mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina
  9. customcondensed
  10. customto give a solid
  11. customThe solid was recrystallized with toluene/methonol, so that 5.8 g of target white powder
  12. customwas obtained in a yield of 92%

出典と根拠

ORDレコード
ord-6f04b398be644656aa03265da7b39083
出典データセット
uspto-grants-2014_10
特許番号
US08859108B2

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