Tris(2-methoxyphenyl)phosphine → 1,6-Di(quinolin-8-yl)pyrene

HRID 2285340노트

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HRID 2285340 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2B(O)O)[CH:4]=[CH:3][CH:2]=1.CCCCCCCC([C:23]([NH3+:42])([C:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=O)C(CCCCCCC)=O)=O.[Cl-].COC1C=CC=CC=1P(C1C=CC=CC=1OC)C1C=CC=CC=1OC.O.C(=O)([O-])[O-].[Na+].[Na+].Br[C:77]1[CH:78]=[C:79]2[C:91]3=[C:92]4[C:82](=[CH:83][C:84](Br)=[CH:85][C:86]4=[CH:87][CH:88]=[C:89]3[CH:90]=1)[CH:81]=[CH:80]2>[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:85]2[C:86]3[C:92]4=[C:91]5[C:89](=[CH:88][CH:87]=3)[CH:90]=[CH:77][C:78]([C:33]3[CH:35]=[CH:36][CH:37]=[C:38]6[C:23]=3[N:42]=[CH:41][CH:40]=[CH:39]6)=[C:79]5[CH:80]=[CH:81][C:82]4=[CH:83][CH:84]=2)[CH:4]=[CH:3][CH:2]=1

참가 물질

9

반응물 5

HCID 78464Tris(2-methoxyphenyl)phosphineHCID 27343808-Quinolineboronic acidHCID 2735133Sodium Carbonate MonohydrateHCID 136154792,7-DibromopyreneHCID 77620884Tricaprylylmethyl ammonium chloride2회

생성물 1

HCID 867117241,6-Di(quinolin-8-yl)pyrene수율 48%

시약·촉매·용매 3

HCID 21218Trioctylmethylammonium chloride촉매HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

Quinoline-8-boronic acid (2.2 g, 12.2 mmol), trioctylmethylammonium chloride (trademark name: Aliquat336 (hereinafter referred to as Aliquat336), prepared by Aldrich Corporation, 0.74 g), palladium acetate (1.3 mg), tris(o-methoxyphenyl)phosphine (13.3 mg), toluene (58 ml), and sodium carbonate water solution (17.8 mmol) were added to dibromo pyrene (2.0 g, 5.6 mmol) synthesized in the prepared example and they were agitated at a temperature of 100° C. of four hours. A crystal was obtained by cooling the resultant reaction liquid at room temperature and filtering the cooled reaction (including the crystal). The compound B of 1.8 g was obtained by washing the crystal in an order of toluene, water, and methanol, and drying the washed crystal under reduced pressure (yield 48%).

후처리

  1. customA crystal was obtained
  2. temperatureby cooling the resultant
  3. customreaction liquid at room temperature
  4. filtrationfiltering
  5. customthe cooled reaction (

출처 및 근거

ORD 기록
ord-22f685f4ef5a431a95a086a1047537dc
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09147846B2

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