Dimethyl Sulfate → Methyl 4-bromo-2-nitrobenzoate

HRID 2191612Notes

Reaction equation

HRID 2191612 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[C:14](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>CC(C)=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:14])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 37744674-Bromo-2-nitrobenzoic acid

Product 1

HCID 18350461Methyl 4-bromo-2-nitrobenzoateYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To acetone 40 mL solution of 4-bromo-2-nitrobenzoic acid 4.0 g were added potassium carbonate 3.4 g and dimethylsulfate 2.3 mL at room temperature, and it was stirred at 50° C. for 1 hour. After the reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure. Water and ethyl acetate were added to the obtained residue. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with saturated sodium hydrogen carbonate aqueous solution,1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure to give methyl 4-bromo-2-nitrobenzoate 4.1 g of white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customthe solvent was removed under reduced pressure
  3. additionWater and ethyl acetate were added to the obtained residue
  4. customThe organic layer was separated
  5. washafter sequential washing with saturated sodium hydrogen carbonate aqueous solution,1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f703885d2434401482ed0a5c7c6351f9
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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