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

HRID 50501

反応式

HRID 50501 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 235060301-(4-Fluorophenoxy)-3-nitrobenzene収率 72%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

EX-634A) Dinitrobenzene (1.68 g, 10 mmol) and 4fluorophenol (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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-1d8ae021c06a4db3b5c2e47c3330c65e
出典データセット
uspto-grants-2004_03
特許番号
US06710089B2

関連ノート

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