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

HRID 1060059

반응식

HRID 1060059 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 110657543-(4-Chloro-3-ethylphenoxy)-1-nitrobenzene수율 78.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
100 °C

실험 절차

EX-8A) 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.

후처리

  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

출처 및 근거

ORD 기록
ord-f27ed7a0f6344a57a081cd61060ee66e
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521607B1

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