Methanol → N-Isopropyl 4-bromo-2-nitroaniline

HRID 1879450Notes

Reaction equation

HRID 1879450 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.[CH:12]([NH2:15])([CH3:14])[CH3:13].CO>ClCCl.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:15][CH:12]([CH3:14])[CH3:13])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6363IsopropylamineHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 2759489N-Isopropyl 4-bromo-2-nitroaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred, cold (0° C.) solution of 4-bromo-1-fluoro-2-nitrobenzene (7 g, 32 mmol) in dichloromethane (100 mL) was added isopropylamine (5 mL, 64 mmol). The mixture was allowed to stir at 0° C. for 3 h and room temperature overnight. It was diluted with water and extracted with CH2Cl2. The organic layer was washed with water and brine, dried (MgSO4), and filtered. The filtrate was concentrated in vacuo to give a crude red solid. Trituration with MeOH afforded the title compound as an orange-red solid. MS (ESI, pos. ion) m/z: 260.7 (M+1).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give a crude red solid

Sources & evidence

ORD record
ord-99b9fbcff799424897ed548cf25fca3c
Source dataset
uspto-grants-2012_11
Patent number
US08314131B2

Reaction notes

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