Sodium Hydroxide → 2,4-Dichloro-5-fluoro-3-methoxynitrobenzene

HRID 47901Notes

Reaction equation

HRID 47901 reaction equation
Br[C:2]1[C:3]([Cl:13])=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[C:6]([F:9])[C:7]=1[Cl:8].[OH-:14].[Na+].[CH3:16][O-].[Na+]>CO>[Cl:13][C:3]1[C:2]([O:14][CH3:16])=[C:7]([Cl:8])[C:6]([F:9])=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 137487963-Bromo-2,4-dichloro-5-fluoronitrobenzene

Product 1

HCID 234317792,4-Dichloro-5-fluoro-3-methoxynitrobenzeneYield 728.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

120 g of 3-bromo-2,4-dichloro-5-fluoronitrobenzene (0.415 mol), 1.66 g of NaOH (0.042 mol) and 26.9 g of sodium methoxide (0.498 mol) in 500 ml of methanol were stirred at 60° C. for 4 hours. The reactant was extracted with ethyl ether, washed successively with water, dilute hydrochloric acid solution, and water, dried over anhydrous sodium sulfate, and evaporated. The residue was recrystallized from ethanol to give 73.5 g of 2,4-dichloro-5-fluoro-3-methoxynitrobenzene (0.306 mol) in 73.8% yield.

Workup

  1. extractionThe reactant was extracted with ethyl ether
  2. washwashed successively with water, dilute hydrochloric acid solution, and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-cee648aa30794c409d9516603b42e638
Source dataset
uspto-grants-2004_03
Patent number
US06699992B2

Reaction notes

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