1-Fluoro-2-nitrobenzene → HCID 28520984, compound

HRID 1748336Notes

Reaction equation

HRID 1748336 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][C:12]([CH3:19])([CH2:17][NH2:18])[CH2:13][N:14]([CH3:16])[CH3:15].CCN(C(C)C)C(C)C>CS(C)=O>[CH3:15][N:14]([CH3:16])[CH2:13][C:12]([CH3:19])([CH3:11])[CH2:17][NH:18][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 104477N,N,2,2-Tetramethylpropane-1,3-diamine

Product 1

HCID 28520984HCID 28520984, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-fluoro-2-nitrobenzene (353 mg, 2.5 mmol) in DMSO (5 mL) is added 2,2,N*1*,N*1*-Tetramethyl-propane-1,3-diamine (391 mg, 3 mmol), followed by Hunig's base (0.65 mL, 3.8 mmol). The reaction flask is sealed and heated to 80° C. for 16 h. The reaction is cooled to room temperature, is poured over ice water and is extracted with CH2Cl2. The organic layer is washed with water, brine, is dried (Na2SO4) and concentrated to afford the title crude compound (635 mg, crude) as an orange oil.

Workup

  1. customThe reaction flask is sealed
  2. temperatureThe reaction is cooled to room temperature
  3. extractionis extracted with CH2Cl2
  4. washThe organic layer is washed with water, brine
  5. dry with materialis dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0b09e8465da54d5999ed1acb117284e6
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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