4-Fluoroaniline → HCID 90388313, compound

HRID 874439Notes

Reaction equation

HRID 874439 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[F:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1>CS(C)=O>[Br:1][C:2]1[C:3]([NH:17][C:16]2[CH:18]=[CH:19][C:13]([F:12])=[CH:14][CH:15]=2)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 2308893-Bromo-2-chloro-5-nitropyridine

Product 1

HCID 90388313HCID 90388313, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

3-Bromo-2-chloro-5-nitropyridine (3.936 g, 16.58 mmol), 4-fluoroaniline (5.53 g, 49.7 mmol) and dimethylsulfoxide (33.2 mL) were combined and stirred at 120° C. for 1 hour. The reaction mixture was cooled to ambient temperature producing a solid. Precipitation was induced further by the addition of 150 mL of water. The solid was collected by filtration and rinsed with 600 mL of water. The solid was purified by flash chromatography (silica gel, 0 to 20% ethyl acetate in heptanes) and then triturated in 15% ethyl acetate in heptanes to give 4.2 g (81%) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customproducing a solid
  3. customPrecipitation
  4. additionwas induced further by the addition of 150 mL of water
  5. filtrationThe solid was collected by filtration
  6. washrinsed with 600 mL of water
  7. customThe solid was purified by flash chromatography (silica gel, 0 to 20% ethyl acetate in heptanes)
  8. customtriturated in 15% ethyl acetate in heptanes

Sources & evidence

ORD record
ord-a8293bb5c7704c33953d706b92a3d3f6
Source dataset
uspto-grants-2015_03
Patent number
US08980879B2

Reaction notes

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