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

HRID 1879449Notes

Reaction equation

HRID 1879449 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Br:8][C:9]1[CH:14]=[CH:13][C:12](F)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1>CS(C)=O>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 24758Sodium hydrideHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 467397914-bromo-N-(tert-butyl)-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of t-butylamine (1.3 mL, 13 mmol) in DMSO (15 mL) was added sodium hydride (60% wt. in mineral oil, 0.53 g, 14 mmol) at RT. After the reaction mixture was stirred for 10 min, it was treated with 1-bromo-4-fluoro-3-nitrobenzene (2.0 mL, 9.1 mmol). The reaction mixture was stirred at RT for 1 h the 70° C. for 3 h. After cooling to RT, it was quenched with 50 mL of water and extracted with DCM (3×40 mL). The combined organic phases were washed with 2 N HCl followed by brine. The resulting organic solution was then dried over magnesium sulfate and concentrated under reduced pressure to give 4-bromo-N-tert-butyl-2-nitrobenzenamine as a red crystalline solid. The crude product was used without further purification. MS (ESI, pos. ion) m/z: 273.9 (M+1).

Workup

  1. stirringThe reaction mixture was stirred at RT for 1 h the 70° C. for 3 h
  2. customit was quenched with 50 mL of water
  3. extractionextracted with DCM (3×40 mL)
  4. washThe combined organic phases were washed with 2 N HCl
  5. dry with materialThe resulting organic solution was then dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-43e91f03917d4d0a9fce02a4707b4d59
Source dataset
uspto-grants-2012_11
Patent number
US08314131B2

Reaction notes

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