Water → 1-Fluoro-5-methoxy-2-methyl-4-nitrobenzene

HRID 419434Notes

Reaction equation

HRID 419434 reaction equation
[F:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[C:13]([O-])([O-])=O.[K+].[K+].IC.O>CN(C)C=O>[CH3:13][O:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]([CH3:12])=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 127824115-Fluoro-4-methyl-2-nitrophenol

Product 1

HCID 184681411-Fluoro-5-methoxy-2-methyl-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Fluoro-4-methyl-2-nitrophenol (2.83 g, 16.5 mmol) was dissolved in N,N-dimethylformamide (25 mL). K2CO3 (3.4 g, 25 mmol) and iodomethane (1.2 mL, 20 mmol) were added and the mixture was stirred at rt overnight. The mixture was then poured into H2O and stirred until solids crashed out. The solids were filtered and air dried to give the title compound without further purification (2.76 g, 90%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.92 (d, J=8.1 Hz, 1H), 7.25 (d, J=11.7 Hz, 1H), 3.89 (s, 3H), 2.19 (d, J=1.5 Hz, 3H).

Workup

  1. stirringstirred until solids
  2. filtrationThe solids were filtered
  3. customair dried

Sources & evidence

ORD record
ord-956b4df23a02461f9c0edf4901dcd1bc
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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