Tert-Butylamine → 5-Bromo-N-tert-butyl-2-nitroaniline

HRID 2370379Notes

Reaction equation

HRID 2370379 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13]>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:16][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:3]=1

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 547590575-Bromo-N-tert-butyl-2-nitroanilineYield 96.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-bromo-2-fluoro-nitrobenzene (4 g, 18.2 mmol) and tert-butylamine (4.78 mL, 45.5 mmol, 2.5 eq) in EtOH (80 mL) is stirred for 15 h at 85° C., allowed to cool and concentrated. The residue purified by silica gel column chromatography (Hex/EtOAc, 1:0→99:1) to afford 4.8 g of the title compound as an orange solid: ESI-MS: 273.0/275.0 [M+H]+; tR=5.68 min (System 1); TLC: Rf=0.49 (Hex/EtOAc, 9:1).

Workup

  1. temperatureto cool
  2. concentrationconcentrated
  3. customThe residue purified by silica gel column chromatography (Hex/EtOAc, 1:0→99:1)

Sources & evidence

ORD record
ord-7fbbbc3dfcf14f2094a439a05ea5ffa4
Source dataset
uspto-grants-2014_04
Patent number
US08710085B2

Reaction notes

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