Isopropanol → 3-Bromo-4-(1-methylethoxy)benzenamine

HRID 2070351Notes

Reaction equation

HRID 2070351 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[CH:5]=[CH:6][C:7]=1F.C(=O)([O-])[O-].[K+].[K+].[CH:18]([OH:21])([CH3:20])[CH3:19]>>[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[O:21][CH:18]([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 696992-Bromo-1-fluoro-4-nitrobenzene

Product 1

HCID 187825223-Bromo-4-(1-methylethoxy)benzenamine

Conditions

Temperature
80 °C

Procedure

3-Bromo-4-fluoronitrobenzene (1.0 eq) was added to a stirring solution of potassium carbonate (2.0 eq) in isopropanol. The solution was heated for 4 days at 80° C. The solution was cooled and filtered through Celite and the plug washed with EtOAc. The organic layer is then washed with brine and water, dried over MgSO4, filtered and concentrated to yield the desired product. Rt=8.72 min.

Workup

  1. temperatureThe solution was cooled
  2. filtrationfiltered through Celite
  3. washthe plug washed with EtOAc
  4. washThe organic layer is then washed with brine and water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-06d1206399a14ae1903d2d5c52b0b003
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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