Dimethyl Sulfate → Methyl 4-bromo-2-nitrobenzoate

HRID 1673329Notes

Reaction equation

HRID 1673329 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+].S(OC)(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 40 mL of acetone solution containing 4.0 g of 4-bromo-2-nitrobenzoic acid, 3.4 g of potassium carbonate and 2.3 mL of dimethyl sulfate were added at room temperature and stirred at 50° C. for 1 hour. After the reaction mixture was cooled to room temperature, the solvent was evaporated under reduced pressure. Water and ethyl acetate were added to the obtained residue. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution, 1.0 mol/L hydrochloric acid and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure to obtain 4.1 g of methyl 4-bromo-2-nitrobenzoate as white solid.

Workup

  1. additionwere added at room temperature
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. customthe solvent was evaporated under reduced pressure
  4. additionWater and ethyl acetate were added to the obtained residue
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. washafter washed with a saturated sodium hydrogen carbonate aqueous solution, 1.0 mol/L hydrochloric acid
  8. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-780c6a1806d24bcbb06b2c81337a0fb2
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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