Methyl iodide → 1-Ethyl-2-methoxy-4-nitrobenzene

HRID 1916368ノート

反応式

HRID 1916368 の反応式
[CH2:1](C1C=CC=CC=1N)C.[CH2:10]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[OH:21])[CH3:11].C([O-])([O-])=O.[K+].[K+].CI>CC(C)=O.O>[CH2:10]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[O:21][CH3:1])[CH3:11]

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 113572-EthylanilineHCID 11430Potassium CarbonateHCID 189800772-Ethyl-5-nitrophenol2 回

生成物 1

HCID 576576411-Ethyl-2-methoxy-4-nitrobenzene

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

Following published procedures 2-ethyl aniline was nitrated (Bergman, J.; Sand, P. Tetrahedron 1990, 46, 1085) and then converted to 2-ethyl-5-nitrophenol (PCT WO 1995/15954). A mixture of 2-ethyl-5-nitrophenol (0.320 g, 1.92 mmol), K2CO3 (0.200 g, 1.44 mmol) and MeI (0.300 g, 2.11 mmol) in acetone (4.0 mL) was heated at 70° C. for 15 h. The solution was cooled to rt, diluted with H2O, concentrated and extracted with CH2Cl2 (3×30 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the title compound (0.347 g) as an orange oil which was used in the next step without further purification. HPLC (Method #1): 3.46 min retention time, (75%); LCMS (ES): m/z 182 [M+H]+.

後処理

  1. temperatureThe solution was cooled to rt
  2. concentrationconcentrated
  3. extractionextracted with CH2Cl2 (3×30 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-b13795afd3654260a7102d7f7fabf91f
出典データセット
uspto-grants-2013_12
特許番号
US08618115B2

反応ノート

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