5-Fluoro-2-methylphenol → 3-Fluoro-6-methyl-2-nitrophenol

HRID 400595ノート

反応式

HRID 400595 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.F[B-](F)(F)F.[O:15]=[N+:16]=[O:17]>C(#N)C.O>[F:1][C:2]1[C:7]([N+:16]([O-:17])=[O:15])=[C:6]([OH:8])[C:5]([CH3:9])=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 27746165-Fluoro-2-methylphenolHCID 11073463Nitronium tetrafluoroborate

生成物 1

HCID 600262953-Fluoro-6-methyl-2-nitrophenol収率 68%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

A stirred solution of 5-fluoro-2-methylphenol (640 mg, 5 mmol) in 20 mL of anhydrous acetonitrile was cooled to −30° C. to −40° C. and treated with nitronium tetrafluoroborate (740 mg, 5.5 mmol). After 45 minutes, the reaction mixture was diluted with 100 mL of cold water and extracted with three 50 mL portions of dichloromethane. The combined organic layers were washed with three 25 mL portions of water, dried over sodium sulfate, and concentrated in vacuo to give a reddish crystalline solid. Chromatography over SiO2 (5% ethyl acetate in hexanes) gave 0.58 g of the title product as bright yellow solid (68% yield).

後処理

  1. extractionextracted with three 50 mL portions of dichloromethane
  2. washThe combined organic layers were washed with three 25 mL portions of water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a reddish crystalline solid

出典と根拠

ORDレコード
ord-837cc21af9e64e5591bc205f022366b6
出典データセット
uspto-grants-2014_06
特許番号
US08741897B2

反応ノート

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