Ethanol → 1-Bromo-6-(naphthalen-1-yl)pyrene

HRID 1852556노트

반응식

HRID 1852556 반응식
[Br:1][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](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[C:19]1(B(O)O)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+].CCO>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[Br:1][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:27]2[C:28]5[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=5)[CH:24]=[CH:25][CH:26]=2)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 176470Pyrene, 1,6-Dibromo-HCID 2545321-Naphthaleneboronic acid

생성물 1

HCID 860841241-Bromo-6-(naphthalen-1-yl)pyrene수율 40%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

A mixture of 18 g (50 mmol) of 1,6-dibromopyrene, 8.6 g (50 mmol) of naphthalen-1-ylboronic acid, 0.6 g (0.5 mmol) of tetrakis(triphenylphosphine) palladium, 38 ml of 2M Na2CO3, 100 ml of EtOH and 200 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 24 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica (hexane-dichloromethane) to give product 8 g (40%) as a white solid.

후처리

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. extractionThe organic layer was extracted with ethyl acetate and water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customthe residue was purified by column chromatography on silica (hexane-dichloromethane)

출처 및 근거

ORD 기록
ord-d1ce880445e64938bc4fb8294826c4d6
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962160B2

반응 노트

불러오는 중…