Nitric Acid → 1-Bromo-4-tert-butyl-2-nitrobenzene

HRID 1507529Notes

Reaction equation

HRID 1507529 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=1>O>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][C:12]=1[N+:6]([O-:9])=[O:7]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 775951-Bromo-4-tert-butylbenzene

Product 1

HCID 112539061-Bromo-4-tert-butyl-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of sulfuric acid (5.79 g, 59.03 mmol, 2.25 equiv) and nitric acid (2.48 g, 39.37 mmol, 1.50 equiv) was added into 1-bromo-4-tert-butylbenzene (5.6 g, 26.28 mmol, 1.00 equiv) while maintaining the temperature below 10° C. The resulting solution was stirred for 20 h at 25° C., poured into water and extracted with ether. The organic phase was dried over anhydrous sodium sulfate. After filtered and concentrated under reduced pressure, the residue was purified through a silica gel column with ethyl acetate/petroleum ether (1:200-1:50) to afford the title compound as a yellow liquid. 1H-NMR (400 MHz, DMSO-d6): δ ppm 1.361(s, 9H), 7.454(dd, J=2.4 Hz, J=8.4 Hz, 1H), 7.65(d, J=8.4 Hz, 1H), 7.848(d, J=2.4 Hz, 1H).

Workup

  1. temperaturewhile maintaining the temperature below 10° C
  2. extractionextracted with ether
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationAfter filtered
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified through a silica gel column with ethyl acetate/petroleum ether (1:200-1:50)

Sources & evidence

ORD record
ord-a3e16a4491724e14bde25feb2a231dc8
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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