Nitric Acid → 4-Bromo-1-ethyl-2-nitrobenzene

HRID 2278403Notes

Reaction equation

HRID 2278403 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH3:9])=[CH:4][CH:3]=1.[N+:10]([O-])([OH:12])=[O:11].O>OS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 153131-Bromo-4-ethylbenzene

Product 1

HCID 75669964-Bromo-1-ethyl-2-nitrobenzeneYield 34.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a solution of 1-bromo-4-ethylbenzene (7 g, 37.8 mmol) in 9 mL concentrated H2SO4 at −20° C. was added a mixture of H2SO4 (3.74 g, 41.9 mmol) and HNO3 (2.64 g, 41.9 mmol). The mixture was stirred at −20° C. for 2 h. Water was added and the mixture was extracted with EtOAc. The organic phase was washed with aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography to give that tile compound (3 g, 34%).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic phase was washed with aqueous NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a859486f0d9346fd85a470936f6d2057
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

Loading…