Toluene → [3'-(3,6-Diphenylcarbazol-9-yl)biphenyl-3-yloxy]methane

HRID 1502190

반응식

HRID 1502190 반응식
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:20]3[CH:19]=[CH:18][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[C:12]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:13]=3)[CH:5]=[CH:6][CH:7]=1.[CH3:33][O:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C(Cl)Cl.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(O)C>[C:27]1([C:12]2[CH:11]=[CH:10][C:9]3[N:8]([C:4]4[CH:5]=[C:6]([C:37]5[CH:38]=[CH:39][CH:40]=[C:35]([O:34][CH3:33])[CH:36]=5)[CH:7]=[CH:2][CH:3]=4)[C:20]4[C:15]([C:14]=3[CH:13]=2)=[CH:16][C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:18][CH:19]=4)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

9

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 581422319-(3-bromophenyl)-3,6-diphenyl-9H-Carbazole

생성물 1

HCID 66717069[3'-(3,6-Diphenylcarbazol-9-yl)biphenyl-3-yloxy]methane수율 85.4%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

The obtained 9-(3-bromophenyl)-3,6-diphenylcarbazole (3.20 g, 6.75 mmol), 3-methoxyphenylboronic acid (1.54 g, 10.1 mmol) and tetrakis(triphenylphosphine)palladium (0.124 g) were added to a solvent mixture of toluene (30 mL) and ethanol (10 mL). Then, an aqueous solution of sodium carbonate (37.3 g) in distilled water (90 mL) was added the mixture. The resultant mixture was refluxed for 9 hours in a nitrogen atmosphere and then cooled to room temperature. The obtained mixture was diluted with methylene chloride and the insoluble matter was removed through filtration. The organic layer was washed with water and separated. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography using as an eluent a solvent mixture of methylene chloride/hexane (2/3 by volume), to thereby obtain 2.89 g of [3′-(3,6-diphenylcarbazol-9-yl)biphenyl-3-yloxy]methane.

후처리

  1. customthe insoluble matter was removed through filtration
  2. washThe organic layer was washed with water
  3. customseparated
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography
  6. additiona solvent mixture of methylene chloride/hexane (2/3 by volume)

출처 및 근거

ORD 기록
ord-31d2d8947f3d4766817a5f37423f0bd2
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206202B2

연결된 노트

불러오는 중…