Ethanol → HCID 68441434、化合物

HRID 525977

反応式

HRID 525977 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10](Br)=[CH:9][CH:8]=3.[CH2:16]([O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[C:34]([O-:37])(O)=O.[Na+].[CH2:39](O)[CH3:40]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH2:16]([O:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:3]=[CH:4][C:5]3[NH:6][C:7]4[C:12]([C:13]=3[CH:14]=2)=[CH:11][C:10]([C:2]2[CH:3]=[CH:4][C:5]([O:37][CH2:34][CH2:9][CH2:8][CH2:7][CH2:12][CH2:11][CH2:39][CH3:40])=[CH:13][CH:14]=2)=[CH:9][CH:8]=4)=[CH:27][CH:26]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

参加物

7

反応物 4

HCID 702EthanolHCID 2748743,6-DibromocarbazoleHCID 516892Sodium BicarbonateHCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)

生成物 1

HCID 68441434HCID 68441434、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

3,6-dibromocarbazole (3.03 g, 9.32 mmol), 4-(octyloxy)phenylboronic acid (7.14 g, 28.5 mmol), aqueous NaHCO3 (80 ml), ethanol (120 ml) and toluene (190 ml) was mixed and degassed with nitrogen for 15 minutes before adding the Pd(PPh3)4 catalyst (80 mg, 0.07 mmol). The reaction mixture was then brought to reflux at 90° C. for 5 h 20 minutes. It was quenched with water when reached room temperature and extracted three times with ethyl acetate. The combined organic phases were washed with brine and water and evaporated. The residual solid was dissolved in toluene and precipitated in petroleum ether. The precipitate was purified using column chromatography with toluene as mobile phase which yielded 3,6-bis(4-(octyloxy)phenyl)-carbazole (5.42 g, 9.41 mmol) as a white solid.

後処理

  1. customdegassed with nitrogen for 15 minutes
  2. customIt was quenched with water when
  3. customreached room temperature
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic phases were washed with brine and water
  6. customevaporated
  7. dissolutionThe residual solid was dissolved in toluene
  8. customprecipitated in petroleum ether
  9. customThe precipitate was purified

出典と根拠

ORDレコード
ord-17a430f12f94472fb301a45aff739f46
出典データセット
uspto-grants-2016_05
特許番号
US09343198B2

関連ノート

読み込み中…