Iodoethane → 1-Ethoxy-5-fluoro-4-methyl-2-nitrobenzene

HRID 419621노트

반응식

HRID 419621 반응식
[CH3:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.I[CH2:14][CH3:15].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:9][CH2:14][CH3:15])=[CH:6][C:7]=1[F:8]

참가 물질

6

반응물 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 127824115-Fluoro-4-methyl-2-nitrophenol

생성물 1

HCID 594528831-Ethoxy-5-fluoro-4-methyl-2-nitrobenzene수율 60.6%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매

실험 절차

4-Methyl-5-fluoro-2-nitrophenol (11.1 g, 65.0 mmol) and iodoethane (12.2 g, 78.0 mmol) were dissolved in 100 mL of DMSO with stirring. K2CO3 (13.5 g, 97.5 mmol) was added. The reaction was stirred for 3 h and then diluted with DCM and filtered. The filtrate was poured into H2O and extracted with DCM. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound of step A (8.0 g, 39.4 mmol) as a pale yellow crystalline solid. 1H NMR (400 MHz, CDCl3) δ 7.76 (d, J=8.1 Hz, 1H), 6.70 (d, J=11.0 Hz, 1H), 4.10 (q, J=7.0 Hz, 2H), 2.22 (s, 3H), 1.45 (t, J=7.0 Hz, 3H).

후처리

  1. stirringThe reaction was stirred for 3 h
  2. filtrationfiltered
  3. additionThe filtrate was poured into H2O
  4. extractionextracted with DCM
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f8596cf6d2564e7abe2e4f04878f3b32
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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