Reaktion #552691

Reaktionsgleichung

urea

sodium persulphate

Nitromethane

sodium hydroxide

sodium 2-bromobenzenesulphinate

→

(2-bromophenylsulphonyl)nitromethane

Ausbeute 0.9%

Lösungsmittel

Ether

acetic acid

dichloromethane

water

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled in an ice bath
2. 2
   SonstigeThe organic phase was separated
3. 3
   Extraktionthe aqueous phase was extracted with ether (150 ml×bb 3)
4. 4
   TrocknenThe combined organic phases were dried (MgSO4)
5. 5
   Sonstigethe solvent was removed by evaporation
6. 6
   SonstigeThe resultant brown solid was purified by MPLC
7. 7
   Wascheneluting with dichloromethane

Vorschrift

Nitromethane (4.6 ml, 82.3 mmol) was added to a stirred solution of sodium hydroxide (7.9 g, 197.5 mmol) in water (50 ml). A solution of sodium 2-bromobenzenesulphinate (20 g, 82.5 mmol) in water (100 ml) was added, followed by dichloromethane (50 ml). The reaction mixture was cooled in an ice bath and a solution of potassium ferricyanide (3 g, 9.1 mmol) in water (20 ml) was added, followed by solid sodium persulphate (12 g, 50.4 mmol). The resultant deep orange solution was allowed to stir for one hour at ambient temperature. Ether (25 ml) was added, followed by urea (5 g), and the pH of the reaction mixture was then adjusted to pH 6 with 20% aqueous acetic acid solution. The organic phase was separated and the aqueous phase was extracted with ether (150 ml×bb 3). The combined organic phases were dried (MgSO4), and the solvent was removed by evaporation. The resultant brown solid was purified by MPLC, eluting with dichloromethane, to give (2-bromophenylsulphonyl)nitromethane as a pale yellow solid (0.197 g), m.p. 74°-76° C.; microanalysis, found: C,29.7; H,2.1; N,4.9%; C7H6BrNO4S requires: C,30.0; H,2.1; N,5.0%.

Quelle