ChemicalBook CAS DataBase List 2-Bromo-3-hydroxypyridine

2-Bromo-3-hydroxypyridine synthesis

11synthesis methods

Product Name:2-Bromo-3-hydroxypyridine
CAS Number:6602-32-0
Molecular formula:C5H4BrNO
Molecular Weight:174

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6602-32-0

The general procedure for the synthesis of 2-bromo-3-hydroxypyridine from 3-hydroxypyridine was as follows: (a) A hypobromite solution was prepared by slowly adding bromine (2.74 mL, 8.49 g, 5.31 mmol) to 10% sodium hydroxide solution (50 mL) at 5°C to 10°C. Subsequently, this hypobromite solution was added dropwise to 10% sodium hydroxide solution (50 mL) containing 3-hydroxypyridine (5.0 g, 52.6 mmol) over 20 minutes. The reaction mixture was continued to be stirred for 30 minutes. The pH of the reaction solution was adjusted to 6-7 with acetic acid. the mixture was cooled to 5°C and maintained for 1 h. The solid product was subsequently collected by filtration. The product was washed with water and dried under vacuum at 85°C to give 2-bromo-3-hydroxypyridine (6.22 g, 67% yield). References: 1) GJ Clark and L W Deedy, Australian J Chem, (1981), 34, 927.

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6602-32-0
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Yield:6602-32-0 94%

Reaction Conditions:

with hydrogen bromide in dichloromethane at 140;Inert atmosphere;

Steps:

2-Bromo-3-hydroxypyridine (22b)

2-bromo-3-methoxypyridine (295 mg, 1.57 mmol) was heated in hydrobromide acid (5 ml) to 140 °C and stirred overnight. The solution was neutralized with a saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic layers were dried over Na₂SO₄ and the solvent was removed under reduced pressure. Yield: 258 mg (94 %), white crystals. ¹H-NMR((CD₃)₂CO, 500 MHz): δH = 9.26 (s, 1H), 7.89 (dd, J = 1.6, 4.4 Hz, 1H), 7.32-7.36 (m,1H), 7.23-7.27 (m, 1H); ¹³C-NMR ((CD₃)₂CO, 125 MHz): δC = 152.4, 142.1, 131.9, 125.3, 124.5.

References:

Hu, Qingzhong;Kunde, Jessica;Hanke, Nina;Hartmann, Rolf W. [European Journal of Medicinal Chemistry,2015,vol. 96,p. 139 - 150] Location in patent:supporting information

109-00-2
607 suppliers
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6602-32-0
422 suppliers
$10.00/1g

References

109-00-2
607 suppliers
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6602-32-0
422 suppliers
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6602-33-1 Synthesis