4-Fluorophenol → 1-(4-Fluorophenoxy)-3-nitrobenzene

HRID 48067

반응식

HRID 48067 반응식
[N+]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11])([O-])=O.[F:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[F:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:9]2[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][CH:8]=2)=[CH:16][CH:15]=1

참가 물질

6

반응물 3

HCID 97324-FluorophenolHCID 107071,2-DinitrobenzeneHCID 10796Cesium carbonate

생성물 1

HCID 235060301-(4-Fluorophenoxy)-3-nitrobenzene수율 72%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

Ex-634A) Dinitrobenzene (1.68 g, 10 mmol) and 4-fluorophenol (1.13 g, 10 mmol) were dissolved in anhydrous dimethylsulfoxide (25 mL), and powdered cesium carbonate (8 g, 24.8 mmol) was added. The mixture was stirred and heated to 100° C. using a reflux condenser under a nitrogen atmosphere. After 16 h, the mixture was diluted with water (120 mL), and the aqueous layer was extracted with diethyl ether (4×60 mL). The combined ether layers were washed with 3% HCl, 5% sodium hydroxide, and water, then dried over anhydrous MgSO4. The ether was removed in vacuo, and the recovered oil was purified by flash column chromatography on silica gel eluting with ethyl acetate in hexane (1:25) to give 1.68 g (69%) of the desired 3-(4-fluorophenoxy)nitrobenzene product as orange crystals, 97% pure by HPLC analysis. MS m/z=234 [M+H]+.

후처리

  1. extractionthe aqueous layer was extracted with diethyl ether (4×60 mL)
  2. washThe combined ether layers were washed with 3% HCl, 5% sodium hydroxide, and water
  3. dry with materialdried over anhydrous MgSO4
  4. customThe ether was removed in vacuo
  5. customthe recovered oil was purified by flash column chromatography on silica gel eluting with ethyl acetate in hexane (1:25)

출처 및 근거

ORD 기록
ord-bfc9d62d1fbe4217874c5f1ae9de0de6
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699898B2

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