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

HRID 400595Notes

Reaction equation

HRID 400595 reaction equation
[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

Participants

5

Reactant 2

HCID 27746165-Fluoro-2-methylphenolHCID 11073463Nitronium tetrafluoroborate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-837cc21af9e64e5591bc205f022366b6
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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