Dihexylamine → 2-fluoro-N,N-di-n-hexyl-4-nitroaniline

HRID 56146

Reaction equation

HRID 56146 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.C([O-])([O-])=O.[K+].[K+].[CH2:18]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CS(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 8920DihexylamineHCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 900241452-fluoro-N,N-di-n-hexyl-4-nitroanilineYield 86%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3,4-difluoronitrobenzene (1.59 g, 10 mmol) in DMSO (15 mL) were added K2CO3 (3.04 g, 22 mmol) and di-n-hexylamine (2.04 g, 11 mmol). The mixture was heated at 90° C. overnight, then cooled to rt, diluted with water (50 mL) and extracted with CH2Cl2 (50 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/CH2Cl2 (V/V)=10:1) to give the title compound as pale yellow oil (2.79 g, 86%).

Workup

  1. temperaturecooled to rt
  2. extractionextracted with CH2Cl2 (50 mL×3)
  3. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography (PE/CH2Cl2 (V/V)=10:1)

Sources & evidence

ORD record
ord-ba52dcdca5224e56bb6328da85a7e25d
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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