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Potassium Carbonate → HCID 72326549, 화합물

HRID 1176967
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HRID 1176967 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)=[O:11])=[O:9])=[CH:4][CH:3]=1.[C:19]([O-:22])([O-])=O.[K+].[K+].[Li+].[Cl-].[CH2:27]([O:39][C:40]1[CH:45]=[CH:44][C:43]([CH:46]=[CH2:47])=[CH:42][C:41]=1[O:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[CH2:49]([O:48][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:9])[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH:47]=[CH:46][C:43]4[CH:44]=[CH:45][C:40]([O:39][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[C:41]([O:22][CH2:19][CH2:59][CH2:58][CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH3:49])[CH:42]=4)=[CH:14][CH:13]=3)=[O:11])=[CH:4][CH:3]=2)[CH:44]=[CH:45][C:40]=1[O:39][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 964304,4'-DibromobenzilHCID 433294Lithium ChlorideHCID 59560832HCID 59560832, 화합물

생성물 1

HCID 72326549HCID 72326549, 화합물수율 75.7%

시약·촉매·용매 3

HCID 74236
Tetrabutylammonium Bromide
촉매
HCID 167845palladium(II) acetate촉매
HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A Schlenk tube was charged with 4,4′-dibromobenzil (1.8 g, 4.9 mmol), K2CO3 (3.38 g, 24.5 mmol), Bu4NBr (1.58 g, 4.9 mmol), LiCl (0.21 g, 4.9 mmol), Pd(OAc)2 (0.11 g, 0.49 mmol), 1,2-bis-dodecyloxy-4-vinyl-benzene (JYC-II-004-A) (5.78 g, 12.2 mmol), and 40 mL of dry DMF. The reaction mixture was heated at 100° C. under Ar over the weekend. The reaction mixture was allowed to cool down to room temperature and extracted with CH2Cl2. The organic phase was washed with H2O and dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica gel, dichloromethane:hexanes=1:2 (v/v), dichloromethane:hexanes=1:1 (v/v)), then dichloromethane:hexanes=3:2 (v/v)) to give a bright yellow solid. The solid was further recrystallized from CH2Cl2/hexanes to give a bright yellow solid (4.27 g, 75.6%).

후처리

  1. temperatureto cool down to room temperature
  2. extractionextracted with CH2Cl2
  3. washThe organic phase was washed with H2O
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customThe crude product was purified by column chromatography (silica gel, dichloromethane:hexanes=1:2 (v/v), dichloromethane:hexanes=1:1 (v/v))
  7. customdichloromethane:hexanes=3:2 (v/v)) to give a bright yellow solid
  8. customThe solid was further recrystallized from CH2Cl2/hexanes

출처 및 근거

ORD 기록
ord-e20a54ff28364db7b40e488c40ecf21a
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07842830B2

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