Sodium Carbonate → 3-(6-phenyldibenzothiophen-4-yl)-9H-carbazole

HRID 64551

反応式

HRID 64551 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[C:15]1([C:21]2[C:29]3[S:28][C:27]4[C:30](B(O)O)=[CH:31][CH:32]=[CH:33][C:26]=4[C:25]=3[CH:24]=[CH:23][CH:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C.C1(C)C=CC=CC=1>[C:15]1([C:21]2[C:29]3[S:28][C:27]4[C:30]([C:2]5[CH:3]=[CH:4][C:5]6[NH:6][C:7]7[C:12]([C:13]=6[CH:14]=5)=[CH:11][CH:10]=[CH:9][CH:8]=7)=[CH:31][CH:32]=[CH:33][C:26]=4[C:25]=3[CH:24]=[CH:23][CH:22]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 80271Tri-o-tolylphosphineHCID 2524463-BromocarbazoleHCID 58309647(6-Phenyldibenzo[b,d]thiophen-4-yl)boronic acid

生成物 1

HCID 666916643-(6-phenyldibenzothiophen-4-yl)-9H-carbazole収率 59%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

In a 50-mL three-neck flask were put 1.0 g (4.1 mmol) of 3-bromocarbazole, 1.2 g (4.1 mmol) of 6-phenyl-4-dibenzothienylboronic acid, and 62 mg (0.20 mmol) of tris(2-methylphenyl)phosphine. To this mixture were added 15 mL of toluene, 5 mL of ethanol, and 5 mL of a 2.0 M aqueous sodium carbonate solution. This mixture was degassed by being stirred while the pressure was reduced. To this mixture was added 9 mg (0.041 mmol) of palladium(II) acetate, and the mixture was stirred at 80° C. for 3 hours under a nitrogen stream. After the stirring, the aqueous layer of this mixture was subjected to extraction with toluene, and the solution of the extract and the organic layer were combined and washed with saturated brine. The organic layer was dried over magnesium sulfate. This mixture was separated by gravity filtration, and the filtrate was concentrated to give a solid. This solid was purified by silica gel column chromatography (developing solvent, toluene:hexane=1:2 and then toluene:hexane=3:2). Addition of ethyl acetate/hexane to the obtained solid was followed by irradiation with ultrasonic waves, and the solid was collected by suction filtration, so that 1.0 g of a white solid which was the object of the synthesis in 59% yield. The synthesis scheme of Step 1 is illustrated in (a-11).

後処理

  1. customIn a 50-mL three-neck flask were put
  2. customThis mixture was degassed
  3. stirringthe mixture was stirred at 80° C. for 3 hours under a nitrogen stream
  4. extractionAfter the stirring, the aqueous layer of this mixture was subjected to extraction with toluene
  5. extractionthe solution of the extract
  6. washwashed with saturated brine
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. customThis mixture was separated by gravity filtration
  9. concentrationthe filtrate was concentrated
  10. customto give a solid
  11. customThis solid was purified by silica gel column chromatography (
  12. additionAddition of ethyl acetate/hexane to the obtained solid
  13. customwas followed by irradiation with ultrasonic waves
  14. filtrationthe solid was collected by suction filtration, so that 1.0 g of a white solid which
  15. customthe object of the synthesis in 59% yield
  16. customThe synthesis scheme of Step 1

出典と根拠

ORDレコード
ord-991e02bfb11e40f19fab66b4a9df6c81
出典データセット
uspto-grants-2016_09
特許番号
US09450188B2

関連ノート

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