Methyl iodide → 4-Bromo-2-nitroanisole

HRID 1363660Notes

Reaction equation

HRID 1363660 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[H-].[Na+].[CH3:14]I>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:14])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 243644-Bromo-2-nitrophenolHCID 24758Sodium hydride

Product 1

HCID 1185334-Bromo-2-nitroanisoleYield 61.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

4-Bromo-2-nitrophenol (1.00 g, 4.59 mmol) was added in small portions to a suspension of sodium hydride (400 mg, 9.17 mmol) in dimethylformamide (12 ml) at room temperature under argon atmosphere, then the mixture was stirred at room temperature for 30 minutes. A solution of methyl iodide (1.30 g, 9.174 mmol) in dimethylformamide (4 ml) was added to this mixture, and stirred at room temperature for 6 hours. The reaction mixture was diluted with water and extracted with diisopropyl ether. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (658 mg, 61.8%) as a pale yellow solid.

Workup

  1. stirringstirred at room temperature for 6 hours
  2. extractionextracted with diisopropyl ether
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8696b08a821249318e162b61f4473fa3
Source dataset
uspto-grants-2011_02
Patent number
US07884234B2

Reaction notes

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