Methyl iodide → 1,3-Dichloro-4-methoxy-2-nitrobenzene

HRID 1771678Notes

Reaction equation

HRID 1771678 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[CH:5]=[CH:4][C:3]=1[OH:12].[C:13]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[Cl:11][C:6]1[CH:5]=[CH:4][C:3]([O:12][CH3:13])=[C:2]([Cl:1])[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 205139322,4-Dichloro-3-nitrophenol

Product 1

HCID 205138861,3-Dichloro-4-methoxy-2-nitrobenzeneYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2,4-dichloro-3-nitro-phenol (600 mg, 2.9 mmol, 1.0 eq) in acetone (30 mL), was added K2CO3 (1.2 g, 8.7 mmol, 3.0 eq) and the solution was stirred at room temperature for 30 min. Methyl iodide (1.2 g, 8.7 mmol, 3.0 eq) was added and the reaction was stirred at room temperature overnight. The reaction was filtered to remove the inorganic salts and the organic phase was evaporated in vacuo to give the title compound (550 mg, 86%).

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. filtrationThe reaction was filtered
  3. customto remove the inorganic salts
  4. customthe organic phase was evaporated in vacuo

Sources & evidence

ORD record
ord-7074dac009fa46b0a988e9fe93fd5563
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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