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

HRID 1014262Notes

Reaction equation

HRID 1014262 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>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12]

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). Potassium carbonate (3.4 g, 25 mmol) and iodomethane (1.2 mL, 20 mmol) were added and the mixture was stirred at room temperature overnight. The mixture was then poured into water and stirred until solids crashed out. The solids were filtered and air dried to give 1-fluoro-2-methyl-5-(methyloxy)-4-nitrobenzene without further purification (2.76 g, 90%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.92 (d, J=8.1 Hz, 1 H), 7.25 (d, J=11.7 Hz, 1 H), 3.89 (s, 3H), 2.19 (d, J=1.5 Hz, 3 H).

Workup

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

Sources & evidence

ORD record
ord-fcbe12ee8bc344bea27e7c7b8081f48f
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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