ChemicalBook CAS DataBase List 8-Bromomethylquinoline

8-Bromomethylquinoline synthesis

5synthesis methods

Product Name:8-Bromomethylquinoline
CAS Number:7496-46-0
Molecular formula:C10H8BrN
Molecular Weight:222.08

611-32-5

7496-46-0

To a pre-dried 300 mL three-necked flask under nitrogen atmosphere were added 8-methylquinoline (10.0 g, 69.8 mmol), benzoyl peroxide (0.843 g, 3.49 mmol) and cyclohexane (150 mL). Under stirring conditions, N-bromosuccinimide (13.6 g, 76.8 mmol) was added in batches. The reaction mixture was refluxed for 10 hours. After completion of the reaction, the reaction mixture was filtered. The filtrate was washed sequentially with saturated aqueous sodium bicarbonate (3 x 100 mL) and brine (100 mL) and then dried with anhydrous sodium sulfate. Subsequently, the solvent was removed by vacuum evaporation. Finally, recrystallization was carried out using ether and hexane to give the light brown solid product 8-bromomethylquinoline (7.1 g, 46% yield).

611-32-5 Synthesis

611-32-5
224 suppliers
$26.00/5g

7496-46-0
169 suppliers
$8.00/100mg

Yield:7496-46-0 82%

Reaction Conditions:

with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in tetrachloromethane for 3 h;Reflux;

Steps:

19.1 8-(bromomethyl)quinoline
8-Methylquinoline (1.00 g, 6.98 mmol) in 110 carbon tetrachloride (20 mL) was added 108 N-bromosuccinimide (1.37 g, 7.69 mmol) and 109 AIBN (115 mg, 0.70 mmol). The reaction mixture was stirred at reflux for 3 hours. The reaction mixture was cooled and carbon tetrachloride was removed under reduced pressure. The residue was purified on an ISCO chromatograph (0-10% ethyl acetate/hexane) to give the 140 product as a white solid (1.26 g, 82%); ¹H NMR (300 MHz) (CDCl₃) δ 9.03-9.01 (m, 1H), 8.18-8.15 (d, 1H), 7.85-7.79 (m, 2H), 7.54-7.43 (m, 2H). 5.25 (s, 2H).

References:

RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY;TAXIS PHARMACEUTICALS, INC.;LaVoie, Edmond J.;Parhi, Ajit K.;Sun, Yangsheng US2019/31624, 2019, A1 Location in patent:Paragraph 0468-0469

FullText

611-32-5 Synthesis

611-32-5
224 suppliers
$26.00/5g