5-Bromonicotinic acid synthesis
- Product Name:5-Bromonicotinic acid
- CAS Number:20826-04-4
- Molecular formula:C6H4BrNO2
- Molecular Weight:202.01
29681-44-5
20826-04-4
General procedure for the synthesis of 5-bromonicotinic acid from methyl 5-bromonicotinate: to a solution of methyl 5-bromonicotinate (500 mg, 2.3 mmol) in tetrahydrofuran (THF, 5 mL) was added an aqueous 1 N sodium hydroxide solution (5 mL, 2.3 mmol). The reaction mixture was stirred at room temperature for 10 min. Subsequently, the reaction solution was acidified to pH 6 with acetic acid and then extracted three times with ethyl acetate. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 5-bromonicotinic acid as a white solid (153 mg, 33% yield).
28733-43-9
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20826-04-4
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Yield:20826-04-4 98%
Reaction Conditions:
with acetic acid;isopentyl nitrite at 80; for 24 h;Inert atmosphere;
Steps:
5-Bromo-3-pyridinecarboxylic acid (12)
5-Bromo-3-pyridinecarboxamide (0.2010 g, 1 mmol) wasdissolved in acetic acid (2 mL), and to the stirring solution was added amyl nitrite (0.40 mL, 3 mmol).The reaction was placed under N2 atmosphere and heated to 80 °C for 24 hours, whereupon thereaction was complete by consumption of starting material by TLC. The solution was condensed andco-evaporated with toluene (2 x 5 mL), then purified via trituration from EtOAc and Hexane. Theresulting suspension was filtered to afford off-white powder (0.1993 g, 0.98 mmol). 1H-NMR (400MHz; MeOD): δ 9.12 (d, J = 1.7 Hz, 1H), 8.93 (d, J = 2.3 Hz, 1H), 8.62 (dd, J = 2.3, 1.7 Hz, 1H); MSm/z 200 (M-, 100%); melting point: 180-183 °C; IR (neat) νmax 3033 (w br, O-H stretch), 1673 (s,C=O stretch), 1287 (acyl C-O), 688 (s, aromatic C-H) cm-1
References:
Potter, Garrett T.;Jayson, Gordon C.;Miller, Gavin J.;Gardiner, John M. [Tetrahedron Letters,2015,vol. 56,# 37,p. 5153 - 5156] Location in patent:supporting information
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20826-04-4
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