1-Bromo-3,5-dinitrobenzene → 1-Bromo-3-methoxy-5-nitrobenzene

HRID 541580Notes

Reaction equation

HRID 541580 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([Br:13])[CH:7]=[C:8]([N+]([O-])=O)[CH:9]=1)([O-:3])=[O:2].[CH3:14][O-:15].[Na+]>CO>[Br:13][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[C:8]([O:15][CH3:14])[CH:7]=1

Participants

4

Reactant 2

HCID 445341-Bromo-3,5-dinitrobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 122990761-Bromo-3-methoxy-5-nitrobenzeneYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

3,5-Dinitrobromobenzene (1.25 g, 5.06 mmol) was stirred in methanol (12 mL) and a solution of sodium methoxide (0.5 M in methanol, 12.6 mL) was added. The mixture was heated to 60° C. for 2 hours and cooled to RT. The mixture was quenched with hydrogen chloride solution (1 N) and extracted with dichloromethane. Evaporation and purification by silica chromatography using ethyl acetate and hexanes gave the desired compound (1.0 g, 80%). LCMS for C7H7BrNO3 (M+H)+: m/z=232.1.

Workup

  1. temperaturecooled to RT
  2. customThe mixture was quenched with hydrogen chloride solution (1 N)
  3. extractionextracted with dichloromethane
  4. customEvaporation and purification by silica chromatography

Sources & evidence

ORD record
ord-32406892114447ee972f47690c555538
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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