Cesium carbonate → 1-{3-Chloro-5-(2-naphthyl)phenyl}-6-(4-methylphenyl)pyrene

HRID 1914402노트

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HRID 1914402 반응식
Cl[C:2]1[CH:3]=[C:4]([C:9]2[C:22]3[C:23]4=[C:24]5[C:19](=[CH:20][CH:21]=3)[CH:18]=[CH:17][C:16]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)=[C:15]5[CH:14]=[CH:13][C:12]4=[CH:11][CH:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][C:33]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[C:22]3[C:23]4=[C:24]5[C:19](=[CH:20][CH:21]=3)[CH:18]=[CH:17][C:16]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)=[C:15]5[CH:14]=[CH:13][C:12]4=[CH:11][CH:10]=2)[CH:3]=[C:2]([C:34]2[CH:33]=[CH:32][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=2)[CH:7]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 2734375(Naphthalen-2-yl)boronic acidHCID 861013811-(3,5-Dichlorophenyl)-6-(4-methylphenyl)pyrene

생성물 1

HCID 861012891-{3-Chloro-5-(2-naphthyl)phenyl}-6-(4-methylphenyl)pyrene수율 37.6%

시약·촉매·용매 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 962Water용매

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온도
90 °C

실험 절차

A mixed solution of 0.88 g of 1-(3,5-dichlorophenyl)-6-(4-methylphenyl)pyrene, 0.35 g of 2-naphthylboronic acid, 2.9 g of cesium carbonate, 58 mg of (tris-t-butylphosphine)tetrafluoroborate, 0.12 g of bis(dibenzylideneacetone)palladium(0) and 20 ml of 1,4-dioxane was heated and stirred under a nitrogen gas stream at 90° C. for 4 hours. The solution was cooled to room temperature and 50 ml of water was poured into the solution, followed by extraction with 100 ml of dichloromethane. The organic layer was washed twice with 20 ml of water, dried over magnesium sulfate and then evaporated. The concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 0.40 g of 1-{3-chloro-5-(2-naphthyl)phenyl}-6-(4-methylphenyl)pyrene.

후처리

  1. temperatureThe solution was cooled to room temperature
  2. extractionfollowed by extraction with 100 ml of dichloromethane
  3. washThe organic layer was washed twice with 20 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe concentrate was purified by silica gel column chromatography
  7. customvacuum-dried

출처 및 근거

ORD 기록
ord-e4a1285f71d74e69856a95424d49a357
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08610345B2

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