Methyl iodide → 1-Fluoro-4-methoxy-5-methyl-2-nitrobenzene

HRID 2064135Notes

Reaction equation

HRID 2064135 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([OH:11])=[C:4]([CH3:12])[CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].CI>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([O:11][CH3:13])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 108210594-Fluoro-2-methyl-5-nitrophenol

Product 1

HCID 598501391-Fluoro-4-methoxy-5-methyl-2-nitrobenzeneYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Fluoro-2-methyl-5-nitrophenol (D16) (0.85 mmol, 145 mg) in dimethylformamide (5 mL) under argon was treated with K2CO3 (0.85 mmol, 117 mg, 1 eq) then methyl iodide (1.7 mmol, 242 mg, 2 eq). The mixture was allowed to stir at room temperature for 1.5 h, concentrated under reduced pressure, treated with 10% Na2CO3 aqueous solution and extracted 3 times with ethyl acetate. Organics were combined, dried on MgSO4 and concentrated under reduced pressure to give the title compound as a bright yellow solid (0.79 mmol, 146 mg, 93% yield). Rt=2.84 min.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiontreated with 10% Na2CO3 aqueous solution
  3. extractionextracted 3 times with ethyl acetate
  4. customdried on MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4bb26f1ed91542b08c7ac4eab84a64bc
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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