Dimethylformamide → 4-chloro-2-fluoro-6-iodo-N-(2-(methylsulfonyl)ethyl)aniline

HRID 1500937Notes

Reaction equation

HRID 1500937 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([I:9])[C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.[CH:11]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH2:12].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>O>[Cl:1][C:2]1[CH:8]=[C:7]([I:9])[C:5]([NH:6][CH2:12][CH2:11][S:13]([CH3:16])(=[O:15])=[O:14])=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 19354Methyl vinyl sulfoneHCID 27736504-Chloro-2-fluoro-6-iodoaniline

Product 1

HCID 899240084-chloro-2-fluoro-6-iodo-N-(2-(methylsulfonyl)ethyl)anilineYield 61.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-chloro-2-fluoro-6-iodoaniline (0.5 g, 1.8 mmol), vinylmethylsulfone (0.2 g, 1.8 mmol), Cs2CO3 (1.17 g, 3.6 mmol) and DMF (15 mL) was heated with stirring at 50° C. overnight. The resulting mixture was poured into water and then extracted with EA (50 mL×3). The combined organic phases were dried over Na2SO4 and then concentrated. The residue was purified by column chromatography (EtOAc:PE=1:40) to give 4-chloro-2-fluoro-6-iodo-N-[2-(methylsulfonyl)ethyl]aniline (0.42 g, yield: 61%).

Workup

  1. temperaturewas heated
  2. extractionextracted with EA (50 mL×3)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (EtOAc:PE=1:40)

Sources & evidence

ORD record
ord-8294b705f80f482e83ed0ecf9fe2cb13
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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