t-Butyl bromide → tert-Butyl 4-bromo-2-nitrobenzoate

HRID 1673330Notes

Reaction equation

HRID 1673330 reaction equation
CN(C)C(=O)C.[Br:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10]([N+:17]([O-:19])=[O:18])[CH:9]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:27]([CH3:30])([CH3:29])[CH3:28]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C.O>[Br:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([O:14][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:13])=[C:10]([N+:17]([O-:19])=[O:18])[CH:9]=1

Participants

8

Reactant 4

HCID 10485t-Butyl bromide2×HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 37744674-Bromo-2-nitrobenzoic acid

Product 1

HCID 26369829tert-Butyl 4-bromo-2-nitrobenzoate

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

To 50 ml, of N, N-dimethylacetamide solution containing 5.0 g of 4-bromo-2-nitrobenzoic acid, 41 g of potassium carbonate, 4.6 g of benzyltriethylammonium chloride and 69 mL of 2-bromo-2-methylpropane were added at room temperature and stirred at 55° C. for 10 hours. After the reaction mixture was cooled to room temperature, 12 mL of 2-bromo-2-methylpropane was added and stirred at 55° C. for 4 hours. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Methanol was added to the obtained residue and solid substances were separated by filtration to obtain 3.0 g of tert-butyl 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. stirringstirred at 55° C. for 4 hours
  4. temperatureAfter the reaction mixture was cooled to room temperature
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. washafter washed with 10% citric acid aqueous solution
  8. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  9. additionMethanol was added to the obtained residue and solid substances
  10. customwere separated by filtration

Sources & evidence

ORD record
ord-a77e30ce03dd4452944ffa5fcd881837
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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