5-Bromopyridine-2-carboxylic acid

white Cryst

4.1.7 Toluene (114 mL) was cooled to -78 °C, n-BuLi (79.7 mL, 127 mmol) was added dropwise at the same temperature followed by 2, 5-dibromopyridine (30 g, 120 mmol) in toluene (60 mL) and stirred for 2 h. The Reaction mixture was bubbled with dry carbon dioxide gas for 1 h at -78 °C. Progress of the reaction was monitored by TLC. On completion of the reaction, reaction contents were warmed to room temperature and toluene was distilled under reduced pressure. Then water (200 mL) was added to the reaction mixture and filtered on celite bed. The filtrate was acidified with diluted HCI solution, solid was precipitated out which was filtered and dried over sodium sulphate to yield 5-bromopicolinic acid (12 g, 47 percent yield) as a brown colored solid.Step 1 General procedure: Ester (FAE, 4a-m, 2a or 2b) (500 mg scale, 1 equiv.) was dissolvedin 6 ml THF at 0 °C in a 25 ml round-bottom flask. ThenNaOH(aq) (5 equiv.) was added dropwise and stirred for 15 h atroom temperature. After starting materials were consumed (byTLC), water (20 ml) was added. The reaction mixture was washedwith ethyl acetate (2 x 20 ml). The aqueous solution was acidified(pH 2-3) with 1 M HCl(aq) causing precipitation of a solid, whichwas filtered and dried under vacuum. Recrystallization in ethanolafford clean compound.Preparation 245-Bromopyridine-2-carboxylic acidAdd 5-bromopicolinonitrile (1 g, 5.46 mmol) to concentrated HC1 (13.4 mL, 139.66 mmol) in a round bottomed flask. Heat the mixture to reflux with stirring overnight. Cool the mixture to room temperature. Filter the resulting white solid, washing with water. Dry the solid under reduced pressure to give 5-bromopyridine-2- carboxylic acid (0.707 g, 64percent) as a white solid. LC-ES/MS m/z 202 [M+H]

5-Bromopyridine-2-carboxylic acid is used as a pharmaceutical intermediate. Store in cool, dry place in a well sealed container. Store away from oxidizing agents.

Molecular Weight:202.01
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:200.94254
Monoisotopic Mass:200.94254
Topological Polar Surface Area:50.2
Heavy Atom Count:10
Complexity:140
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes