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Phenylacetyl chloride → 1-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl]-2-phenyl ethanone

HRID 2172364
ノート
印刷プレビュー

反応式

HRID 2172364 の反応式
[CH:1]1[C:6]2=[C:7]3[C:15](=[CH:16][CH:17]=[C:5]2[CH:4]=[CH:3][CH:2]=1)[C:14]1[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:8]3.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:22][C:23]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[C:24]=1[C:25](Cl)=[O:26].[C:34]1([CH2:40][C:41](Cl)=[O:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[CH2:17]([CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][N:8]1[C:7]2[C:15](=[CH:16][C:17]([C:25](=[O:26])[C:24]3[C:23]([CH3:22])=[CH:31][C:30]([CH3:32])=[CH:29][C:28]=3[CH3:33])=[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:6]3=2)[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([C:41](=[O:42])[CH2:40][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:13]=2)[CH3:16]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7679Phenylacetyl chlorideHCID 9196Benzo[a]carbazoleHCID 970382,4,6-Trimethylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride2 回

生成物 1

HCID 866905311-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl]-2-phenyl ethanone収率 159.5%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

To 11H-benzo[a]carbazole (1.06 g, 3.23 mmol) in CH2Cl2 (5 ml) are added AlCl3 (0.510 g, 3.82 mmol) and 2,4,6-trimethylbenzoyl chloride (0.59 g, 3.24 mmol) at 0° C. After stirring at room temperature for 1 hour, AlCl3 (0.51 g, 3.82 mmol) and phenylacetyl chloride (0.52 g, 3.39 mmol) are added at 0° C. The reaction mixture is stirred at room temperature for 2 hours, and then it is poured into ice-water. The crude product is extracted with CH2Cl2, and washed with water and brine. After drying over MgSO4 and concentration, the product is reprecipitated from CH2Cl2 and n-hexane to obtain a white powder (1.53 g, 81%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.79-0.91 (m), 1.18-1.50 (m), 2.19 (s), 2.28 (m), 2.41 (s), 4.38 (s), 4.74 (m), 6.97 (s), 7.22-7.36 (m), 7.56 (d), 7.71 (t), 7.77 (t), 8.14 (d), 8.35 (s), 8.62 (d), 8.63 (s), 9.58 (s).

後処理

  1. stirringThe reaction mixture is stirred at room temperature for 2 hours
  2. extractionThe crude product is extracted with CH2Cl2
  3. washwashed with water and brine
  4. dry with materialAfter drying over MgSO4 and concentration
  5. customthe product is reprecipitated from CH2Cl2 and n-hexane

出典と根拠

ORDレコード
ord-2708f94ef57847c0879d48675562135a
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09051397B2

反応ノート

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