Reaktion #7834

Reaktionsgleichung

3-chloro-4-methylbenzoic acid

N-bromosuccinimide

benzoyl peroxide

→

4-(bromomethyl)-3-chlorobenzoic acid

Lösungsmittel

CCl4

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 2.5 h
2. 2
   EinengenThe mixture was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONdissolved in MTBE
4. 4
   WaschenThe organic mixture was washed with 1N NaOH (3×25 mL)
5. 5
   Extraktionextracted with CH2Cl2 (3×25 mL)
6. 6
   TrocknenThe combined organic layers were dried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

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.

Quelle