Tert-Butylamine → 4-bromo-N-(tert-butyl)-2-nitroaniline

HRID 1966665Notes

Reaction equation

HRID 1966665 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 467397914-bromo-N-(tert-butyl)-2-nitroanilineYield 109.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-bromo-1-fluoro-2-nitrobenzen (25 g, 0.1 mol) in THF (100 mL) is added t-butylamine (18 mL, 0.17 mol). The solution is heated at 60° C. for 16 hours. The solvent is removed in vacuum. The residue is suspended in methanol (20 mL). The precipitate is collected by filtration and washed with methanol to give (4-bromo-2-nitro-phenyl)-tert-butyl-amine as an orange solid (30 g, 97%).

Workup

  1. customThe solvent is removed in vacuum
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with methanol

Sources & evidence

ORD record
ord-2f7febab1bc447d9acb3053f6e8396ef
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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