Methyl iodide → 5-Fluoro-2-nitroanisole

HRID 419328Notes

Reaction equation

HRID 419328 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[OH:11])([O-:3])=[O:2].IC.[C:14]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:14][O:11][C:5]1[CH:6]=[C:7]([F:10])[CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 27792505-Fluoro-2-nitroanisoleYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-nitro-5-fluoro-phenol (56.0 g, 357 mmol) and iodomethane (24.5 mL, 393 mmol) in DMF (200 mL) was added K2CO3 (54.2 g, 393 mmol). Significant bubbling occurred. The mixture was stirred at rt overnight. The mixture was poured into H2O (800 mL) and the H2O washed with diethyl ether (3×200 mL). The ether washes were combined and washed with H2O (2×400 mL). The ether layer was dried (MgSO4), filtered, and rotovaped down to give the title compound (56.0 g, 327 mmol, 92%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.96-7.90 (m, 1H), 6.79-6.67 (m, 2H), 3.93 (s, 3H).

Workup

  1. customSignificant bubbling
  2. additionThe mixture was poured into H2O (800 mL)
  3. washthe H2O washed with diethyl ether (3×200 mL)
  4. washwashed with H2O (2×400 mL)
  5. dry with materialThe ether layer was dried (MgSO4)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-389dd89490ad4b40aaa3622466038989
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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