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

HRID 1916368노트

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HRID 1916368 반응식
[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]

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 113572-EthylanilineHCID 11430Potassium CarbonateHCID 189800772-Ethyl-5-nitrophenol2회

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-b13795afd3654260a7102d7f7fabf91f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618115B2

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