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Potassium Carbonate → HCID 72326549、化合物

HRID 1176967
ノート
印刷プレビュー

反応式

HRID 1176967 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 964304,4'-DibromobenzilHCID 433294Lithium ChlorideHCID 59560832HCID 59560832、化合物

生成物 1

HCID 72326549HCID 72326549、化合物収率 75.7%

試薬・触媒・溶媒 3

HCID 74236
Tetrabutylammonium Bromide
触媒
HCID 167845palladium(II) acetate触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e20a54ff28364db7b40e488c40ecf21a
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07842830B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート