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

HRID 525885

反応式

HRID 525885 の反応式
[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]

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 677643-Fluorocatechol

生成物 1

HCID 27589791-Fluoro-2,3-dimethoxybenzene収率 84.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-590ab0175ed64104a24f886df0608776
出典データセット
uspto-grants-2016_05
特許番号
US09340556B2

関連ノート

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