Quinoline, 8-bromo-5,6,7,8-tetrahydro- synthesis

Yield:125163-08-8 66%

Reaction Conditions:

with N-Bromosuccinimide;azobisisobutyronitrile in tetrachloromethane at 20; for 12 h;Irradiation;

Steps:

8-Bromo-5,6,7,8-tetrahydroquinoline (2x):

General procedure: To a rt solution of 2-propylpyridine (2.5 g, 20.63 mmol) and (E)-2,2'-(diazene-1,2-diyl)bis(2-methylpropanenitrile)(1.253 g, 7.63 mmol) in CCl₄ (60 mL) was added N-bromosuccinimide(1.933 mL, 22.69 mmol). The mixture was stirred under fluorescent light at rt for 12 h. The precipitates were filtered off through a pad of celite, washed with CCl₄ (10 mL). The organic solutions were combined. After removal of the organic solvent under reduced pressure, purification of the residue by flash chromatography on silica gel with 0-20% EtOAc/Hexanes provided the title compound 2d as a pale yellow liquid (3.18 g, 77%).

References:

Yu, Ming;Stevenson, Karis;Zhou, Gene [Tetrahedron Letters,2014,vol. 55,# 41,p. 5591 - 5594] Location in patent:supporting information