2,4-Difluoroaniline → HCID 90387152, compound

HRID 874455Notes

Reaction equation

HRID 874455 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]=[C:18]([F:20])[CH:17]=[CH:16][C:14]=1[NH2:15]>CS(C)=O>[Br:1][C:2]1[C:3]([NH:15][C:14]2[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:13]=2[F:12])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 97092,4-DifluoroanilineHCID 2308893-Bromo-2-chloro-5-nitropyridine

Product 1

HCID 90387152HCID 90387152, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-2-chloro-5-nitropyridine (2.374 g, 10 mmol) and 2,4-difluoroaniline (2.58 g, 20 mmol) in dimethylsulfoxide (20 mL) was heated at 100° C. for 2 hours. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate filtered, and concentrated. The residue was purified on silica gel eluting with 1:20 ethyl acetate/heptanes to give the title compound (1.75 g, 5.30 mmol, 53.0% yield) as yellow crystals.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with additional ethyl acetate twice
  5. washThe combined organic layers were washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel eluting with 1:20 ethyl acetate/heptanes

Sources & evidence

ORD record
ord-6a08e673fd6d484ba2fb0ceaf6d93773
Source dataset
uspto-grants-2015_03
Patent number
US08980879B2

Reaction notes

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