Reaction #60496

Reaction equation

nitric acid

4-bromo-1,2-dimethoxybenzene

→

title compound

1-Bromo-4,5-dimethoxy-2-nitrobenzene

Solvents

acetic acid

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was warmed to 15° C.
2. 2
   workup.STIRRINGstirring
3. 3
   TemperatureThe reaction mixture was cooled to 0° C.
4. 4
   workup.STIRRINGstirred
5. 5
   Extractionextraction
6. 6
   Washwashed with water
7. 7
   DryingAfter drying the organic layer over anhydrous magnesium sulfate
8. 8
   Filtrationthe desiccant was filtered off
9. 9
   Concentrationthe filtrate was concentrated under reduced pressure
10. 10
    OtherThe obtained crude product
11. 11
    Otherwas recrystallized from ethanol

Procedure

A mixture of concentrated nitric acid (14 mL) and acetic acid (42 mL) was cooled to 10° C. while stirring, and then 4-bromo-1,2-dimethoxybenzene (2 g, 9.21 mmol) was gradually added to the stirred mixture. The reaction mixture was warmed to 15° C., and stirring was continued for 60 minutes. The reaction mixture was cooled to 0° C. and stirred while adding ice water, and then extraction was performed with ether. The obtained organic layer was neutralized with saturated aqueous solution of sodium hydrogencarbonate and potassium carbonate, and then washed with water. After drying the organic layer over anhydrous magnesium sulfate, the desiccant was filtered off and the filtrate was concentrated under reduced pressure. The obtained crude product was recrystallized from ethanol to give 2.09 g of the title compound as light yellow crystals.

Source