Reaction #684980

Reaction equation

N-bromosuccinimide

N-dodecanoyl-4-methylbenzenesulfonamide

Ethyl acetate

heptane

→

4-bromomethyl-N-(dodecanoyl)benzenesulfonamide

Yield 120.2%

Solvents

tetrachloromethane

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was heated for 1 h to 80° C
2. 2
   TemperatureThe reaction mixture was heated another 2 h to 80° C
3. 3
   OtherThe solid was removed by filtration
4. 4
   OtherThe solvent was removed from the filtrate

Procedure

At 80° C., N-bromosuccinimide (1.43 g, 8.06 mmol) and dibenzoylperoxide (62 mg, 0.25 mmol) were added successively to a solution of N-dodecanoyl-4-methylbenzenesulfonamide (3 g, 8.48 mmol) in tetrachloromethane (75 ml). The reaction mixture was heated for 1 h to 80° C. Another portion of dibenzoylperoxide (100 mg, 0.41 mmol) was added. The reaction mixture was heated another 2 h to 80° C. It was cooled to room temperature and left for 16 h. Ethyl acetate (100 ml) and heptane (100 ml) were added. The solid was removed by filtration. The solvent was removed from the filtrate to give 4.19 g of crude 4-bromomethyl-N-(dodecanoyl)benzenesulfonamide, which was used for the next step, without further purification.

Source