1,3-Dinitrobenzene → 3-(4-Chloro-3-ethylphenoxy)-1-nitrobenzene

HRID 1005993

反応式

HRID 1005993 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 110657543-(4-Chloro-3-ethylphenoxy)-1-nitrobenzene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

EX-18A) 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-290cbc155ef14d4e836072db5448a329
出典データセット
uspto-grants-2004_09
特許番号
US06787570B2

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