Methyl iodide → 1-Bromo-5-fluoro-4-methoxy-2-methylbenzene

HRID 529414노트

반응식

HRID 529414 반응식
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.[C:11](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([O:9][CH3:11])=[CH:6][C:7]=1[CH3:8]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 108997434-Bromo-2-fluoro-5-methylphenol

생성물 1

HCID 227282131-Bromo-5-fluoro-4-methoxy-2-methylbenzene수율 91.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

4-Bromo-2-fluoro-5-methylphenol (40 g, 0.19 mol), cesium carbonate (75 g, 0.23 mol), and iodomethane (15 ml, 0.23 mol) were combined in 100 ml of DMF and stirred at RT for one hour (exothermic). The solution was diluted with ethyl acetate and filtered. The solution was washed with water twice, dried with anhydrous sodium sulfate, filtered, and concentrated. The product was purified via silica gel column chromatography (RediSep 330 g column) using 0-50% ethyl acetate in hexane to afford 1-bromo-5-fluoro-4-methoxy-2-methylbenzene (38 g, 89% yield) as a colorless liquid. No [M+H] peak by LCMS. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.24 (s, 3 H) 3.76 (s, 3 H) 6.73 (d, J=8.80 Hz, 1 H) 7.13 (d, J=10.56 Hz, 1 H)

후처리

  1. filtrationfiltered
  2. washThe solution was washed with water twice
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified via silica gel column chromatography (RediSep 330 g column)

출처 및 근거

ORD 기록
ord-fcffb780bad24fd6b9522ba514240085
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346827B2

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