Dichloromethane → 1-(3-t-Butylphenyl)-6-(4-methylphenyl)pyrene

HRID 1027323ノート

反応式

HRID 1027323 の反応式
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[C:25]([C:29]1[CH:30]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:32]=[CH:33][CH:34]=1)([CH3:28])([CH3:27])[CH3:26].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.CN(C)C=O>[C:25]([C:29]1[CH:30]=[C:31]([C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[CH:11]=[CH:10][C:9]([C:18]3[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)[CH:32]=[CH:33][CH:34]=1)([CH3:26])([CH3:27])[CH3:28]

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 222401372-(3-(tert-Butyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 861013611-Bromo-6-(4-methylphenyl)pyrene

生成物 1

HCID 866430241-(3-t-Butylphenyl)-6-(4-methylphenyl)pyrene収率 81.7%

試薬・触媒・溶媒 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Next, a mixed solution of 4.6 g of 1-bromo-6-(4-methylphenyl)pyrene, 4.9 g of 2-(3-t-butylphenyl)-4,4,5,5-tetramethyl 1,3,2-dioxaborolane, 8.0 g of tripotassium phosphate, 306 mg of PdCl2(dppf).CH2Cl2 and 75 ml of deaerated dimethylformamide was heated with stirring under a nitrogen gas flow at 100° C. for 6 hours. After cooling to room temperature, 100 ml of water was injected, followed by extraction with 100 ml of dichloromethane. The organic layer was washed twice with 50 ml of water, dried over magnesium sulfate and then evaporated. The resultant concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 4.3 g of 1-(3-t-butylphenyl)-6-(4-methylphenyl)pyrene.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionfollowed by extraction with 100 ml of dichloromethane
  3. washThe organic layer was washed twice with 50 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. concentrationThe resultant concentrate
  7. customwas purified by silica gel column chromatography
  8. customvacuum-dried

出典と根拠

ORDレコード
ord-d8980f36b56f42aea53219552aa6cbc0
出典データセット
uspto-grants-2014_05
特許番号
US08729530B2

反応ノート

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