ChemicalBook CAS DataBase List 2,6-DIBROMO-3-HYDROXYPYRIDINE

2,6-DIBROMO-3-HYDROXYPYRIDINE synthesis

8synthesis methods

Product Name:2,6-DIBROMO-3-HYDROXYPYRIDINE
CAS Number:6602-33-1
Molecular formula:C5H3Br2NO
Molecular Weight:252.89

109-00-2
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$10.00/10g

6602-33-1
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$14.00/250mg

Yield: 46%

Reaction Conditions:

with bromine;sodium hydroxide at 0 - 20; for 5 h;

Steps:

40
5.40
2,6-Dibromopyridin-3-ol (30)
An ice-cold solution of bromine (16.2 mL, 315 mmol) in sodium hydroxide (2.5 M, 320 mL, 800 mmol) was added dropwise to a stirred solution of pyridin-3-ol (10.0 g, 105 mmol) in sodium hydroxide (2.5 M, 110 mL, 275 mmol).
The solution was stirred at 0 °C for 1 h and then at room temp for 4 h.
A small amount of precipitate that formed was removed by filtration.
The filtrate was cooled, and concentrated hydrochloric acid was added until the pH reached 1.
The solid was collected by filtration, washed with water, dried, and recrystallised from carbon tetrachloride to give 30 (12.1 g, 46%) as a beige coloured solid: ¹H NMR (400 MHz, DMSO-d₆) δ = 11.14 (br s, 1H), 7.47 (d, J = 8.0 Hz, 1H), 7.26 (d, J = 8.0 Hz, 1H); MS ES-ve m/z 250, 252, 254 (M-H)^-.

References:

Miah, Afjal H.;Abas, Hossay;Begg, Malcolm;Marsh, Benjamin J.;O'Flynn, Daniel E.;Ford, Alison J.;Percy, Jonathan M.;Procopiou, Panayiotis A.;Richards, Steve A.;Rumley, Sally-Anne [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 15,p. 4298 - 4311]

109-00-2
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$10.00/10g

6602-32-0 Synthesis