Reacción #352404

Ecuación de reacción

N-tert-butyl-2-methoxycarbonyl-5-methylbenzenesulfonamide

N-bromosuccinimide

→

N-tert-butyl-5-bromomethyl-2-methoxycarbonylbenzenesulfonamide

Rendimiento 59.9%

Disolventes

tetrachloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 6-8 h under a nitrogen protective-gas atmosphere
2. 2
   Otrowith simultaneous irradiation with a daylight lamp
3. 3
   FiltraciónThe solution is then filtered
4. 4
   Lavadowashed in succession with sodium disulphide solution, sodium hydrogen carbonate solution and water
5. 5
   Secadodried over Na2SO4
6. 6
   Otroevaporated to dryness i.v
7. 7
   OtroCrystallization of the residue from diisopropyl ether/ethyl acetate

Procedimiento

A solution of 54.8 g (192 mmol) of N-tert-butyl-2-methoxycarbonyl-5-methylbenzenesulfonamide in 420 ml of tetrachloromethane is heated at reflux for 6-8 h under a nitrogen protective-gas atmosphere, following addition of 36 g (202 mmol) of N-bromosuccinimide and 0.5 g of azobisisobutyronitrile (AIBN) with simultaneous irradiation with a daylight lamp. The solution is then filtered and then washed in succession with sodium disulphide solution, sodium hydrogen carbonate solution and water, dried over Na2SO4 and evaporated to dryness i.v. Crystallization of the residue from diisopropyl ether/ethyl acetate yields 41.9 g (57%) of N-tert-butyl-5-bromomethyl-2-methoxycarbonylbenzenesulfonamide of mp. 88°-90° C.

Fuente