Water → 2,3-Difluoro-6-nitroanisole

HRID 1014240Notes

Reaction equation

HRID 1014240 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[OH:12].[C:13](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[F:8][C:7]1[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[C:3]([O:12][CH3:13])[C:2]=1[F:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27337452,3-Difluoro-6-nitrophenol

Product 1

HCID 27827542,3-Difluoro-6-nitroanisoleYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,3-difluoro-6-nitrophenol (15.01 g, 85.8 mmol) in anhydrous dimethylformamide (120 mL) was cautiously added potassium carbonate (16.6 g, 120 mmol) and methyl iodide (6.63 mL, 107 mmol). The resulting suspension was stirred overnight. The next morning the reaction was poured into water and extracted twice with diethyl ether. The organic layers were washed twice with 5% LiCl, dried over sodium sulfate. The solvents were removed under reduced pressure to afford 1,2-difluoro-3-(methyloxy)-4-nitrobenzene as a yellow oil (14.7 g, 91% yield). 1H NMR (400 MHz, CDCl3) δ ppm 4.13 (s, 3 H), 7.00 (td, J=9.07, 7.15 Hz, 1 H), 7.67 (ddd, J=9.35, 5.32, 2.20 Hz, 1 H).

Workup

  1. extractionextracted twice with diethyl ether
  2. washThe organic layers were washed twice with 5% LiCl
  3. dry with materialdried over sodium sulfate
  4. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-4cf9147838b84eb28bbfc4220915a375
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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