تفاعل #48214

معادلة التفاعل

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

N-bromo-succinimide

dibenzoylperoxide

water

→

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

المذيبات

carbon tetrachloride

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةto reflux for 2 h (TLC monitored)
3. 3
   أخرىThe organic layer was separated
4. 4
   غسيلwashed with brine (20 mL)
5. 5
   تجفيفdried over sodium sulphate
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe residue was purified by column chromatography (EtOAc:hexane, 1:25, Rf: 0.28)

الإجراء التجريبي

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%.

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