Hydrochloric Acid → 5-Bromo-2-isopropoxy-4-methyl-phenylamine

HRID 388555Notes

Reaction equation

HRID 388555 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH:12]([CH3:14])[CH3:13])=[CH:4][C:3]=1[CH3:15].Cl>C(O)C.[Fe]>[Br:1][C:2]1[C:3]([CH3:15])=[CH:4][C:5]([O:11][CH:12]([CH3:13])[CH3:14])=[C:6]([NH2:8])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 597645931-Bromo-4-isopropoxy-2-methyl-5-nitro-benzene

Product 1

HCID 597644885-Bromo-2-isopropoxy-4-methyl-phenylamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 702EthanolSolvent

Procedure

To 1-Bromo-4-isopropoxy-2-methyl-5-nitro-benzene from the previous step (0.734 g, 2.68 mmol) and iron (powder, 325 mesh, 1.05 g) in 20 mL ethanol is added 1 mL of 1N aqueous HCl with cooling in an ice bath. Following this addition, the reaction is heated at reflux for 2 hrs. Then an additional 0.5 g of iron is added and the reaction is heated at reflux for an additional 2 hrs. The reaction mixture is cooled down and filtered though a pad of Celite. The filtrate is concentrated in vacuo, affording 5-Bromo-2-isopropoxy-4-methyl-phenylamine as an orange oil. The product is used for the next step without further purification.

Workup

  1. temperaturewith cooling in an ice bath
  2. additionthis addition
  3. temperaturethe reaction is heated
  4. temperatureat reflux for 2 hrs
  5. temperaturethe reaction is heated
  6. temperatureat reflux for an additional 2 hrs
  7. temperatureThe reaction mixture is cooled down
  8. filtrationfiltered though a pad of Celite
  9. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-d8d3450dfed14c1f9bf00a636c28860c
Source dataset
uspto-grants-2013_02
Patent number
US08377921B2

Reaction notes

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