ChemicalBook CAS DataBase List 5-Bromopyridine-2-carbaldehyde

5-Bromopyridine-2-carbaldehyde synthesis

8synthesis methods

Product Name:5-Bromopyridine-2-carbaldehyde
CAS Number:31181-90-5
Molecular formula:C6H4BrNO
Molecular Weight:186.01

624-28-2

68-12-2

31181-90-5

5-Bromo-2-pyridinecarboxaldehyde was synthesized according to General Method C using 2,5-dibromopyridine and N,N-dimethylformamide (DMF) as raw materials. The specific operation was as follows: 2,5-dibromopyridine (237 mg, 1 mmol) was mixed with DMF (115 μL, 1.5 mmol) for the reaction. After completion of the reaction, the crude product was purified by fast column chromatography (eluent: hexane/ethyl acetate = 10:1) to afford the target compound 5-bromo-2-pyridinecarboxaldehyde (27b) as a brown solid (149 mg, 80% yield). Thin layer chromatography (TLC) analysis showed an Rf value of 0.45 (Expander: hexane/ethyl acetate = 8:1). Nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 400 MHz, CDCl3) data were as follows: δ 10.03 (1H, s), 8.85 (1H, dd, J = 0.8, 2.0 Hz), 8.02 (1H, ddd, J = 0.8, 2.0, 8.0 Hz), 7.85 (1H, dd, J = 0.8, 8.0 Hz). The nuclear magnetic resonance carbon spectrum (13C NMR, 100 MHz, CDCl3) data were as follows: δ 192.4, 151.7, 151.3, 140.0, 126.3, 122.8. The spectral data obtained were in agreement with literature reports.

97483-77-7 Synthesis

97483-77-7
566 suppliers
$10.00/5g

31181-90-5
369 suppliers
$5.00/250mg

Yield:31181-90-5 60%

Reaction Conditions:

with diisobutylaluminium hydride in tetrahydrofuran at -78; for 4 h;

Steps:

159.1 Step 1:
To a stirred solution of 5-bromopicolinonitrile (0.5 g, 2.732 mmol, 1.0 eq) in tetrahydrofuran (10 mL) at -78 °C DIBAL (4 mL, 4.98 mmol, 1.5 eq) was added and reaction mixture was stirred for 4 h at -78 °C. The reaction mixture was monitored by TLC, and quenched with 2N HCI (2 mL) and extracted with dichloromethane (10 mL), dried over sodium sulphate and evaporated to provide fairly pure 5-bromopicolinaldehyde (0.3 g, ~ 60 %) which was used to the next stage without further purification.

References:

GRüNENTHAL GMBH;FRANK, Robert;BAHRENBERG, Gregor;CHRISTOPH, Thomas;LESCH, Bernhard WO2013/13815, 2013, A1 Location in patent:Page/Page column 228

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3430-13-5 Synthesis