methyl 3-bromo-4-methyl-5-nitropicolinate Chemical Properties

Boiling point:

377.2±42.0 °C(Predicted)

Density 

1.668

storage temp. 

2-8°C

pka

-4.11±0.10(Predicted)

methyl 3-bromo-4-methyl-5-nitropicolinate Usage And Synthesis

Preparation

Methyl-3-bromo-4-methyl-5-nitropicolinate synthesis: 3-bromo-2-iodo-4-methyl-5-nitropyridine (129.0 g, 0.38 mol) and (Ph3P)2PdCl2 (7.92 g, 3 mol%) were suspended in CH3CN (1300 mL) and MeOH (430 mL) and Et3N (79.3 mL, 1.5 eq) was added. The mixture was transferred to a steel 5000 mL pressure vessel, 4 bar of CO pressure was applied and the reaction mixture was slowly heated to 80 oC. Subsequently, it was stirred for 5 h at this temperature, then allowed to cool overnight. The volatiles were removed in vacuo, the residue was stirred in EtOAc (1000 mL) and filtered. The residue was extracted with EtOAc (2*250 mL) and the combined filtrates were washed with brine (1000 mL) and dried on Na2SO4. The volatiles were removed in vacuo, affording 120 g of a brown oil. This was coated on 120 g of silicagel and purified by column chromatography (3500 g of silica gel, EtOAc/heptane 1:3, KMnO4 staining). The appropriate fractions were combined and concentrated to give Methyl-3-bromo-4-methyl-5-nitropicolinate as a beige solid (63.5 g, 61%).

methyl 3-bromo-4-methyl-5-nitropicolinate(1150618-07-7)Related Product Information

• Methyl 3-bromo-L-phenylalaninate
• Methyl 3-bromo-L-phenylalaninate hydrochloride
• Methyl 3-BroMo-5-forMylbenzoate