Sodium Hydroxide → 2-Fluoro-4-(methylsulphonyl)aniline

HRID 532466Notes

Reaction equation

HRID 532466 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[CH3:10][S:11]([O-:13])=[O:12].[Na+].N1CCC[C@H]1C(O)=O.[OH-].[Na+]>[Cu]I.O.CS(C)=O>[F:9][C:4]1[CH:3]=[C:2]([S:11]([CH3:10])(=[O:13])=[O:12])[CH:8]=[CH:7][C:5]=1[NH2:6]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 1230504-Bromo-2-fluoroanilineHCID 145742L-ProlineHCID 2733271Sodium methanesulfinate

Product 1

HCID 27833852-Fluoro-4-(methylsulphonyl)anilineYield 99.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

4-bromo-2-fluoroaniline (10.0 g, 52.62 mmol, 1.0 eq), sodium methansulfinate (9.5 g, 1.5 eq), copper(I) iodide (1.0 g, 0.1 eq), L-Proline (1.2 g, 0.2 eq) and sodium hydroxide (0.4 g, 0.2 eq) were placed in a sealed tube, and dimethylsulfoxide (100 mL) was added thereto. The reaction mixture was stirred at 90° C. for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and water was added thereto, followed by extraction three times with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting compound was purified using column chromatography (MC:MeOH=50:1) to obtain the title compound (9.9 g).

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. extractionfollowed by extraction three times with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting compound was purified

Sources & evidence

ORD record
ord-6fd7cf263b304f94946dc6680b95114b
Source dataset
uspto-grants-2014_10
Patent number
US08853213B2

Reaction notes

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