Methyl iodide → 1-Fluoro-2,3-dimethoxybenzene

HRID 525885

반응식

HRID 525885 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1O.[C:10](=[O:13])([O-])[O-].[K+].[K+].I[CH3:17]>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:17])[C:3]=1[O:13][CH3:10]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 677643-Fluorocatechol

생성물 1

HCID 27589791-Fluoro-2,3-dimethoxybenzene수율 84.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 3-fluorobenzene-1,2-diol (145 g, 1132 mmol), potassium carbonate (313 g, 2264 mmol) and iodomethane (177 mL, 2830 mmol) in N,N-Dimethylformamide (DMF) (300 mL) was stirred at RT for 48 h. LCMS showed the complete consuption of starting material. The mixture was diluted with ethyl acetate (EA), filtered, washed with water, dried and evaporated in vacuo. The crude material was purified by normal phase automatic silica gel column chromatography (Combiflash RF, 220 g column), eluting with EA/Hexane (10%-80%) to afford 1-fluoro-2,3-dimethoxybenzene (149 g, 954 mmol, 84% yield) as a colorless oil. LCMS (M+H)+: 157.0.

후처리

  1. filtrationfiltered
  2. washwashed with water
  3. customdried
  4. customevaporated in vacuo
  5. customThe crude material was purified by normal phase automatic silica gel column chromatography (Combiflash RF, 220 g column)
  6. washeluting with EA/Hexane (10%-80%)

출처 및 근거

ORD 기록
ord-590ab0175ed64104a24f886df0608776
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340556B2

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