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

HRID 400595노트

반응식

HRID 400595 반응식
[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

참가 물질

5

반응물 2

HCID 27746165-Fluoro-2-methylphenolHCID 11073463Nitronium tetrafluoroborate

생성물 1

HCID 600262953-Fluoro-6-methyl-2-nitrophenol수율 68%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-837cc21af9e64e5591bc205f022366b6
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741897B2

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