1-Bromo-4-tert-butyl-2-nitrobenzene → 3-tert-Butylaniline

HRID 1859531Notes

Reaction equation

HRID 1859531 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[N+:12]([O-])=O.[H][H]>[Pd].CO>[C:8]([C:5]1[CH:4]=[C:3]([NH2:12])[CH:2]=[CH:7][CH:6]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 2

HCID 112539061-Bromo-4-tert-butyl-2-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 793343-tert-Butylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Bromo-4-tert-butyl-2-nitro-benzene (18 g) was reduced as described in General Method 3 using 10% palladium on charcoal (1 g) and MeOH (100 mL) in a hydrogen atmosphere (50 psi). The catalyst was filtered, and the solvents were evaporated. The residue was taken in EtOAc (100 mL) and washed with saturated sodium bicarbonate solution and H2O. The solution was dried and concentrated. The residue was purified by flash chromatography to give 3-tert-butyl-phenylamine. MS (APCI): 150 (M+H).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvents were evaporated
  3. washwashed with saturated sodium bicarbonate solution and H2O
  4. customThe solution was dried
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-10a94bc5a0604676870016b3681d7e2b
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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