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

HRID 1914402ノート

反応式

HRID 1914402 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e4a1285f71d74e69856a95424d49a357
出典データセット
uspto-grants-2013_12
特許番号
US08610345B2

反応ノート

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