Toluene → 9-[Bis(4-methylphenyl)amino]phenyl-10-bromoanthracene

HRID 132509

반응식

HRID 132509 반응식
Br[C:2]1[C:3]2[C:8]([C:9]([Br:16])=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([N:24](C2C=CC(B(O)O)=CC=2)[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1.[C:41]1(C)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.C(O)C>[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)[C:2]2[C:3]3[C:8]([C:9]([Br:16])=[C:10]4[C:15]=2[C:14]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:13][CH:12]=[CH:11]4)=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:22][CH:23]=1

참가 물질

9

반응물 4

HCID 1140TolueneHCID 10340Sodium Carbonate2회HCID 682269,10-DibromoanthraceneHCID 23083792[4-[Bis(4-methylphenyl)amino]phenyl]boronic acid

생성물 1

HCID 866013499-[Bis(4-methylphenyl)amino]phenyl-10-bromoanthracene

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

In a nitrogen flow, 1 g (2.98 mmol) of 9,10-dibromoanthracene and 1.44 g (4.46 mmol) of bis(4-methylphenyl)aminobenzene-4-boronic acid were dissolved and stirred in a deaerated mixture solvent of 100 ml of toluene and 50 ml of ethanol, followed by dropping a sodium carbonate aqueous solution prepared by dissolving 9 g of anhydrous sodium carbonate in 45 ml of water. After stirring the mixture for 30 minutes, 257 mg (0.223 mmol) of tetrakis(triphenylphosphine)palladium was added thereto. Then, the mixture was heated and stirred for about 3 hours in an oil bath heated at 80° C. After returning the reaction solution to room temperature, 40 ml of water and 50 ml of ethyl acetate were added thereto and the resultant solution was then separated into an aqueous layer and an organic layer. Furthermore, the aqueous layer was extracted with toluene and ethyl acetate, and was then combined with the previous organic layer and dried with magnesium sulfate. The solvent was evaporated and then the residue was purified by silicagel-column chromatography (toluene:hexane=1:2) to obtain 1.13 g of 9-[bis(4-methylphenyl)amino]phenyl-10-bromoanthracene.

후처리

  1. customprepared
  2. temperatureThen, the mixture was heated
  3. stirringstirred for about 3 hours in an oil bath
  4. customto room temperature
  5. customthe resultant solution was then separated into an aqueous layer
  6. extractionFurthermore, the aqueous layer was extracted with toluene and ethyl acetate
  7. dry with materialdried with magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was purified by silicagel-column chromatography (toluene:hexane=1:2)

출처 및 근거

ORD 기록
ord-54ef8cedab1c4634807a5cf24457e021
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07387845B2

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