Reacción #7834

Ecuación de reacción

3-chloro-4-methylbenzoic acid

N-bromosuccinimide

benzoyl peroxide

→

4-(bromomethyl)-3-chlorobenzoic acid

Disolventes

CCl4

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 2.5 h
2. 2
   ConcentraciónThe mixture was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONdissolved in MTBE
4. 4
   LavadoThe organic mixture was washed with 1N NaOH (3×25 mL)
5. 5
   Extracciónextracted with CH2Cl2 (3×25 mL)
6. 6
   SecadoThe combined organic layers were dried over MgSO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated

Procedimiento

A solution of 3-chloro-4-methylbenzoic acid (5.0 g, 29 mmol), N-bromosuccinimide (5.7 g, 32 mmol), benzoyl peroxide (710 mg, 2.9 mmol) in CCl4 (300 mL) was heated at reflux for 2.5 h. The mixture was concentrated under reduced pressure and dissolved in MTBE. The organic mixture was washed with 1N NaOH (3×25 mL). The aqueous mixture was acidified with 1N HCl to pH 2 and extracted with CH2Cl2 (3×25 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to afford 4-(bromomethyl)-3-chlorobenzoic acid.

Fuente