5-Bromo-3-pyridinol

Light yellow needles

A solution of 3-bromo-5-methoxy-pyridine (33 18.8 g, 0.1 mol), HBr (80 mL, 48percent) and glacial HOAc (60 mL) was stirred overnight at 120° C. Hydrobromic acid (60 mL, 48percent) was added slowly to replace evaporated solvents and stirred at 120° C. for overnight. The reaction mixture was cooled to RT and then poured into the ice. The pH was adjusted to about 6 by adding 6N NaOH and then extracted with EtOAc (2.x.200 mL). The organic layer was dried over NaStep 2 Using reported procedures, 3, 5-dibromopyridine 1 (5 g, 21 mmol) was dissolved in 100 mL anhydrous methanol (Figure 2). The solution was cooled to OReference Example 35 Example 40A 3-(Benzyloxy)-5-bromopyridine (15.0 g, 56.8 mmol), prepared as described in (U.S. Pat. No. 5, 733, 912), and 30percent HBr/HOAc (200 mL) were stirred at ambient temperature for 16 hours. The reaction mixture was diluted with diethyl ether (500 mL) and the resulting white solid (12.9 g) was isolated by filtration. The solid, in methanol (300 ml), was treated with concentrated NH4OH (50 mL). After stirring at ambient temperature for 12 hours, the reaction mixture was concentrated under reduced pressure to provide the title compound (9.8 g, 89percent) as a white solid. MS (DCI/NH3) m/z 174, 176 (M+H)+.3-Benzyloxy-5-bromopyridine (15.0 g, 56.8 mmol), prepared as described in (US 5, 733, 912), and 30percent HBr/acetic acid (200 mL) were stirred at ambient temperature for 16 hours. The reaction was diluted with diethyl ether (500 mL) and the resulting white solid (12.9 g) was isolated by filtration. The solid was taken up in methanol (300 mL) and concentrated NH4OH (50 mL) was added. After stirring at ambient temperature for 12 hours, the mixture was concentrated under reduced pressure to provide the title compound as a white solid (9.8 g, 89percent). MS (DCI/NH3) m/z 174/176 (M+H)+.

Molecular Weight:174.00
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:172.94763
Monoisotopic Mass:172.94763
Topological Polar Surface Area:33.1
Heavy Atom Count:8
Complexity:78.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes