Nitric Acid → 4-Bromo-3-nitroaniline

HRID 1915465Notes

Reaction equation

HRID 1915465 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1>OS(O)(=O)=O.C(Cl)Cl>[Br:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][C:7]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 78074-Bromoaniline

Product 1

HCID 6122994-Bromo-3-nitroaniline

Reagents, catalysts & solvents 1

HCID 86615737H2SO4 CH2Cl2Solvent

Conditions

Temperature
20 °C

Procedure

Conc. nitric acid (15.8 mL, 376.9 mmol) was added to a solution of 4-bromoaniline (40 g, 232.5 mmol) in H2SO4/CH2Cl2 (400 mL, 1:1, v/v) dropwise at 0° C. under an atmosphere of N2. The cooling bath was removed and the mixture was stirred at 20° C. until the starting material was consumed (about 1 h). The reaction mixture was poured onto water and neutralized with NaOH solution to pH=9 and extracted with DCM. The organic layer was dried, filtered and evaporated in vacuo to afford the crude product 4-bromo-3-nitro-aniline, which was used directly in the next step.

Workup

  1. customdropwise at 0° C.
  2. customThe cooling bath was removed
  3. customwas consumed (about 1 h)
  4. additionThe reaction mixture was poured onto water and neutralized with NaOH solution to pH=9
  5. extractionextracted with DCM
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-a6ee1526b0ad45edaf68e04619943414
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

Loading…