Methyl 6-bromopicolinate synthesis
- Product Name:Methyl 6-bromopicolinate
- CAS Number:26218-75-7
- Molecular formula:C7H6BrNO2
- Molecular Weight:216.03
67-56-1
21190-87-4
26218-75-7
The general procedure for the synthesis of methyl 6-bromo-2-pyridinecarboxylate from methanol and 6-bromo-2-pyridinecarboxylic acid is as follows: 1. 6-bromo-2-pyridine carboxylic acid (6.000 g) was dissolved in methanol (180 mL) containing concentrated hydrochloric acid and heated to reflux. 2. Sulfuric acid (2 mL) was added and the reaction continued to reflux for 4 hours. 3. Upon completion of the reaction, the reaction mixture was cooled to about 0°C and concentrated. 4. Ammonia (4.8 mL) was added to the concentrated mixture. 5. The resulting solution was evaporated to give a white solid residue. 6. 6. The white solid was dissolved in a solvent mixture of dichloromethane (100 mL) and brine (100 mL), and the organic layer was separated with sufficient shaking. 7. The organic layer was dried with magnesium sulfate and the solvent was evaporated to give the white solid product methyl 6-bromo-2-pyridinecarboxylate (6.300 g, 98% yield). Product characterization data: 1H NMR (400 MHz, CDCl3) δ 4.00 (3H, s), 7.66-7.74 (2H, m), 8.07-8.13 (1H, m).
21190-87-4
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26218-75-7
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Yield:26218-75-7 90%
Reaction Conditions:
with methanol;sulfuric acidHeating / reflux;
Steps:
19
To a solution of 6-bromopicolinic acid (2.5 g) in MeOH (100 mL) was added concentrated H2SO4 (5 mL). The reaction was refluxed until the 6-bromopicolinic acid was gone. The mixture was dried by evaporation and then purified by silica gel column chromatography (ISCO) to give compound 19A (ca 90% yield). LC/MS: m/z 216/218 (M+H+).
References:
Li, James J,;Hamann, Lawrence G.;Ruan, Zheming;Cooper, Christopher B.;Wu, Shung C.;Simpkins, Ligaya M.;Wang, Haixia;Nayeem, Akbar;Krystek, Stanley R. US2006/235028, 2006, A1 Location in patent:Page/Page column 32
67-56-1
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21190-87-4
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$10.00/5g
26218-75-7
241 suppliers
$9.00/1g
21190-87-4
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$10.00/5g
74-88-4
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26218-75-7
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67-56-1
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34160-40-2
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26218-75-7
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626-05-1
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26218-75-7
241 suppliers
$9.00/1g