1,3-Dinitrobenzene → HCID 11065754、化合物

HRID 392950

反応式

HRID 392950 の反応式
[N+]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1)([O-])=O.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=1[CH2:21][CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:4]2[CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:8][CH:9]=2)=[CH:16][C:15]=1[CH2:21][CH3:22]

参加物

5

反応物 3

HCID 74521,3-DinitrobenzeneHCID 10796Cesium carbonateHCID 842234-Chloro-3-ethylphenol

生成物 1

HCID 11065754HCID 11065754、化合物収率 78.5%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 1,3-dinitrobenzene (16.8 g, 0.1 mol) and 4-chloro-3-ethylphenol (15.6 g, 0.1 mol) in 200 mL of dimethylsulfoxide was added cesium carbonate (65 g, 0.2 mol). The reaction mixture was heated at 100° C. under nitrogen overnight then cooled to room temperature. The reaction mixture was filtered through celite then rinsed with diethyl ether and a small amount of water. The filtrate was extracted several times with diethyl ether. The organic layers were combined, washed with water and brine, dried over MgSO4, and concentrated in vacuo to give 21.8 g (78%) of the desired 3-(4-chloro-3-ethylphenoxy)-1-nitrobenzene product as a dark orange oil, which was greater than 90% pure by reverse phase HPLC analysis. HRMS calcd. for C14H12ClNO3: 295.0849 [M+NH4]+, found 295.0862.

後処理

  1. temperaturethen cooled to room temperature
  2. filtrationThe reaction mixture was filtered through celite
  3. washthen rinsed with diethyl ether
  4. extractionThe filtrate was extracted several times with diethyl ether
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-eed0cba086644f6b95d2b608dbbb453b
出典データセット
uspto-grants-2004_10
特許番号
US06803388B2

関連ノート

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