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ChemicalBook CAS DataBase List 5-BROMO-2-(4-FLUOROPHENYL)PYRIDINE

5-BROMO-2-(4-FLUOROPHENYL)PYRIDINE synthesis

3synthesis methods
-

Yield:463336-07-4 90%

Reaction Conditions:

with palladium diacetate;potassium carbonate;triphenylphosphine in methanol;acetonitrile at 50; for 24 h;Inert atmosphere;regioselective reaction;Suzuki Coupling;

Steps:

Typical procedure for the 2-arylation of 2,5- and 2,3-dibromopyridines

General procedure: 2,5-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid (67 mg, 0.55 mmol), K2CO3 (0.14 g, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (26 mg, 10 mol %) were dissolved in CH3CN/CH3OH (2:1, 6 mL). The solution was stirred at 50 °C under nitrogen atmosphere for 24 h and then cooled and the solid was filtered off. The filtrate was then concentrated and the resulting crude product was dissolved in CH2Cl2 (10 mL). The solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give the desired product 3a (114 mg, 97%) as a white solid.

References:

Zhou, Qizhong;Zhang, Bin;Su, Liangjun;Jiang, Tiansheng;Chen, Rener;Du, Tieqi;Ye, Yuyuan;Shen, Jianfen;Dai, Guoliang;Han, Deman;Jiang, Huajiang [Tetrahedron,2013,vol. 69,# 51,p. 10996 - 11003]