7-Bromoquinolin-8-ol synthesis
- Product Name:7-Bromoquinolin-8-ol
- CAS Number:13019-32-4
- Molecular formula:C9H6BrNO
- Molecular Weight:224.05
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13019-32-4
The general procedure for the synthesis of 5,7-dibromo-8-hydroxyquinoline and 7-bromo-8-hydroxyquinoline from 8-hydroxyquinoline was as follows: bromination was carried out according to the method described in the literature [19]. This was done as follows: 8-hydroxyquinoline (2 mmol, 1 eq.) was dissolved in distilled CHCl3 (15 mL) at room temperature and protected from light, followed by the slow addition of different equivalents of molecular bromine (dissolved in CHCl3) over a period of 10 min. The reaction mixture was stirred continuously for 2 days, during which the progress of the reaction was monitored by TLC. Upon completion of the reaction, the organic layer was washed with 5% NaHCO3 solution (3 x 20 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. Finally, the target product was separated by alumina column chromatography with ethyl acetate/hexane (1:5, 150 mL) as eluent.
148-24-3
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13019-32-4
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Yield: 85%
Reaction Conditions:
with N-Bromosuccinimide in chloroform at 0 - 40; for 18 h;
Steps:
Synthesis of 7-bromoquinolin-8-ol (2)
To a stirred solution of quinolin-8-ol (1) (5 g, 1 mmol) in chloroform (10 mL), N-bromo succinimide (6.13 g, 1 mmol) was added portion wise at 0 °C, slowly raising the temperature to 40 °C and stirred for 18 h. The progress of the reaction was monitored by TLC using ethyl acetate and hexane as an eluent (1:9). After completion of the reaction, the reaction mixture was evaporated under vacuum and washed with water to give the crude 7-bromoquinolin-8-ol (2) (6.53 g), which was then washed with hexane and diethyl ether to yield 7-bromoquinolin-8-ol as a white solid in 85% yield. m.p: 138-143 °C; EI-MS: m/z (%): 224 (M+ H (100)), 145 (32).
References:
Krishna, Palaa [Phosphorus, Sulfur and Silicon and the Related Elements,2018,vol. 193,# 10,p. 685 - 690]
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13019-32-4
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521-74-4
176 suppliers
$5.00/100mg
13019-32-4
58 suppliers
$23.00/250mg