Réaction #48214

Équation de réaction

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

N-bromo-succinimide

dibenzoylperoxide

water

→

Benzoic Acid 5-bromomethyl-2-fluoro-phenyl Ester

Solvants

carbon tetrachloride

diethyl ether

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureto reflux for 2 h (TLC monitored)
3. 3
   AutreThe organic layer was separated
4. 4
   Lavagewashed with brine (20 mL)
5. 5
   Séchagedried over sodium sulphate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutreThe residue was purified by column chromatography (EtOAc:hexane, 1:25, Rf: 0.28)

Mode opératoire

A mixture of benzoic acid 2-fluoro-5-methyl-phenyl ester (CAB02145, 2.47 g, 10.0 mmol), N-bromo-succinimide (1.96 g, 11.0 mmol) and dibenzoylperoxide (10 mg) in carbon tetrachloride (25 mL) was heated to reflux for 2 h (TLC monitored). 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, 1:25, Rf: 0.28). Yield: 1.80 g (58%), white solid. 1H-NMR (400 MHz, CDCl3) δ=4.48 (s, 2H, —CH2Br), 7.18 (dd, J=9.8, 8.6 Hz, 1H), 7.28 (ddd, J=8.6, 4.3, 2.3 Hz, 1H), 7.34 (dd, J=7.0, 2.3 Hz, 1H), 7.50-7.55 (m, 2H), 7.64-7.69 (m, 1H), 8.18-8.23 (m, 2H). LRMS (FAB+): 229.1 (95), 309.0 (100, [M+]+). Found: C, 54.1, H, 3.22%; C14H10BrFO2 (309.13) requires C, 54.39, H, 3.26%.

Source