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Published TCIMAIL newest issue No.198
Maximum quantity allowed is 999
We are proud to present the Ullmann-type coupling reaction of 3-bromoquinoline and 1-butanol using N,N'-bis(2-phenyl-1-naphthyl)-1,2-benzenediamine as a catalytic ligand. This reaction has the advantage of proceeding at room temperature.
3-Bromoquinoline (300 mg, 1.44 mmol), 1-butanol (160 µL, 1.73 mmol), N,N'-bis(2-phenyl-1-naphthyl)-1,2-benzenediamine (74.0 mg, 144 µmol), copper(I) iodide (13.7 mg, 72.1 µmol) and sodium tert-butoxide (277 mg, 2.88 mmol) were dissolved in DMSO (2 mL) and stirred at room temperature for 1.5 hours. The reaction was quenched with water and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane = 0:100 - 5:95) to give 3-butoxyisoquinoline as a yellow oil (227 mg, 78% yield).
The reaction mixture was monitored by NMR.
The reaction was carried out under a nitrogen atmosphere.
3-Butoxyisoquinoline
1H NMR (270 MHz, CDCl3); δ 8.65 (d, J = 3.0 Hz, 1H), 8.02 (dd, J = 6.8, 1.1 Hz, 1H), 7.70 (dd, J = 6.2, 1.9 Hz, 1H), 7.56-7.45 (m, 2H) 7.35 (d, J = 2.7 Hz, 1H), 4.07 (t, J = 6.5 Hz, 2H), 1.90-1.79 (m, 2H), 1.60-1.47 (m, 2H), 0.99 (t, J = 7.6 Hz, 3H).