1-Bromo-3,5-dinitrobenzene → ar-Bromo-ar-nitrobenzenamine

HRID 64083

Reaction equation

HRID 64083 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1>C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1)[NH2:8]

Participants

4

Reactant 1

HCID 445341-Bromo-3,5-dinitrobenzene

Product 1

HCID 44535ar-Bromo-ar-nitrobenzenamineYield 80%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 1-bromo-3,5-dinitrobenzene (20 g, 80.97 mmol) in acetic acid (120 ml) at 90° C. was added iron powder (11.3 g, 202.4 mmol, 2.5 eq) slowly portionwise over a period of 30 min (caution: highly exothermic reaction). After completion of the addition, the mixture was quenched by the addition of crushed ice. The precipitate formed was filtered and was washed with cold water to obtain orange solid. The solid was dried under vacuum to give the product in 80% yield (14 g). 1H NMR (300 MHz, CDCl3): δ 10.55 (br s, 2H), 8.46 (s, 1H), 8.19 (s, 1H), 8.02 (s, 1H).

Workup

  1. customhighly exothermic reaction)
  2. additionAfter completion of the addition
  3. customthe mixture was quenched by the addition of crushed ice
  4. customThe precipitate formed
  5. filtrationwas filtered
  6. washwas washed with cold water
  7. customto obtain orange solid
  8. customThe solid was dried under vacuum
  9. customto give the product in 80% yield (14 g)

Sources & evidence

ORD record
ord-753a8f480966446dafb69e87c8975f55
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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