반응 #48201

반응 방정식

benzoic acid 2-chloro-5-methyl-phenyl ester

N-bromo-succinimide

dibenzoyl peroxide

water

→

Benzoic Acid 5-bromomethyl-2-chloro-phenyl ester

용매

carbon tetrachloride

diethyl ether

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도to reflux for 1 hour (TLC-control)
3. 3
   workup.ADDITIONwere added
4. 4
   기타The organic layer was separated
5. 5
   세척washed with brine (20 mL)
6. 6
   건조dried over sodium sulphate
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residue was purified by column chromatography (EtOAc:hexane, 1:40, Rf: 0.21)
9. 9
   workup.WAITYield: 2.012 g (62%) colourless oil, which solidified after a few hours

실험 절차

A mixture of benzoic acid 2-chloro-5-methyl-phenyl ester (CAB02124, 2.47 g, 10.0 mmol), N-bromo-succinimide (1.96 g, 11.0 mmol) and dibenzoyl peroxide (10 mg) in carbon tetrachloride (25 mL) was heated to reflux for 1 hour (TLC-control). After cooling to room temperature water (50 mL) and diethyl ether (100 mL) were added. The organic layer was separated, washed with brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc:hexane, 1:40, Rf: 0.21). Yield: 2.012 g (62%) colourless oil, which solidified after a few hours (contains ca. 10% benzoic acid 5-dibromomethyl-2-chloro-phenyl ester).

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