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

HRID 2191613Notes

Reaction equation

HRID 2191613 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 bromideHCID 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 N,N-dimethylacetamide 50 mL solution of 4-bromo-2-nitrobenzoic acid 5.0 g were added potassium carbonate 41 g, benzyltriethylammonium chloride 4.6 g and 2-bromo-2-methylpropane 69 mL at room temperature and it was stirred at 55° C. for 10 hours. After the reaction mixture was cooled to room temperature,2-bromo-2-methylpropane 12 mL was added to it, and it was stirred at 55° C. for 4 hours. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Methanol was added to the obtained residue, solid matter was filtrated to give tert-butyl 4-bromo-2-nitrobenzoate 3.0 g of white solid.

Workup

  1. additionwas added to it, and it
  2. stirringwas stirred at 55° C. for 4 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. washafter sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution
  6. customthe solvent was removed under reduced pressure
  7. additionMethanol was added to the obtained residue, solid matter
  8. filtrationwas filtrated

Sources & evidence

ORD record
ord-3cd4972926604f3db895b3810c401772
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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