Monoperoxyphthalic Acid Magnesium Salt → 4-Fluoro-1-methylsulfinyl-2-nitrobenzene

HRID 25459

Reaction equation

HRID 25459 reaction equation
C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:5].[Mg+2].[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=1>CO.ClCCl>[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:23])=[O:5])=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=1

Participants

5

Reactant 2

HCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 127009114-Fluoro-1-(methylsulfanyl)-2-nitrobenzene

Product 1

HCID 225673464-Fluoro-1-methylsulfinyl-2-nitrobenzeneYield 63%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

4-Fluoro-1-methylsulfinyl-2-nitrobenzene can be obtained in the following way: 4.7 g of magnesium monoperoxyphthalate are added portionwise to a solution, under argon, of 1.9 g of 4-fluoro-1-methylsulfanyl-2-nitrobenzene in 6 ml of methanol and 30 ml of dichloromethane. The reaction mixture is then stirred at a temperature in the region of 20° C. for 3 hours, and is then filtered through sintered glass and the solid is washed with dichloromethane. The filtrate is washed with an aqueous sodium hydrogencarbonate solution then with water, dried over magnesium sulfate, treated with 3S black, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue thus obtained is purified by chromatography on a column of 125 g of silice (particle size 40-63 μm), eluting with pure dichloromethane. The fractions containing the expected product are pooled and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 1.3 g of 4-fluoro-1-methylsulfinyl-2-nitrobenzene are thus obtained in the form of a yellow foam (Rf=0.23, silica gel thin layer chromatography, eluent: dichloromethane/ethyl acetate 90/10)).

Workup

  1. filtrationis then filtered through sintered glass
  2. washthe solid is washed with dichloromethane
  3. washThe filtrate is washed with an aqueous sodium hydrogencarbonate solution
  4. dry with materialwith water, dried over magnesium sulfate
  5. additiontreated with 3S black
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  8. customThe residue thus obtained
  9. customis purified by chromatography on a column of 125 g of silice (particle size 40-63 μm)
  10. washeluting with pure dichloromethane
  11. additionThe fractions containing the expected product
  12. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-d3701a554f694506a5dba40497c51f19
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Linked notes

Loading…