2-Bromomethylquinoline

General procedure: 2-Methylquinoline derivatives (0.5mmol), cuprous halide (0.75mmol), TBHP (8.0 eq., 70percent aqueous solution) and CHGeneral procedure: 2-Methylquinolines 1(2 mmol), TBAI (2 mmol), urea (2 mmol), 1, 2-dibromoethane (6 mL), andacetonitrile (6 mL) were mixed in a microwave tube. The reaction mixture was stirred at 95 °C for 30 min under microwave irradiation using a CEM Discover microwave reactor (the highest power: 150 W; run time: 5 min; holdtime: 30 min; temperature: 95 °C). The resulting reaction mixture was concentrated in vacuo, and the crude residue was purified by flash chromatography on silica gel using hexane/EtOAc as eluent.General procedure: The respective 2-methylquinoline (14–20mmol) was dissolved in carbon tetrachloride or benzene (1.3–13.5ml per mmol) and N-bromosuccinimide (1.1 eqv) was added. The mixture was refluxed in the presence of benzoyl peroxide (0.8–1.7mmol) for the indicated below amount of time. After cooling to room temperature, the precipitated succinimide was filtered off and after evaporation af the volatiles under vacuum, the product was purified by flash chromatography.Selective bromination of the2-methyl quinoline (3.0 g, 32.2 mmol) with 1.5 equivalents of NBSin CCl4 for 12 h afforded 1.3 g of compound 1 in 23.2percent yield asyellow solid. The solid was characterized by 1H NMR (Figure S-1)(300 MHz, in ppm CDCl3): d 8.187–8.159 (d, J = 8.4 Hz, 1H), 8.104–8.076 (d, J = 8.4 Hz, 1H), 7.832–7.804 (d, J = 8.4 Hz, 1H), 7.770–7.714(m, 1H), 7.589–7.538 (t, J = 8.4 Hz, 2H), 4.730 (s, 2H). 13C NMR(Figure S-2) (75 MHz, CDCl3): d 156.86, 147.50, 137.25, 129.92, 129.25, 127.50, 127.43, 127.31, 127.00, 121.13, 34.37.2-(bromomethyl)quinoline. Quinolin-2-ylmethanol 7 (6 g, 37.8 mmol) was dissolved in CHPREPARATION 302-(Bromomethyl)quinolineThe title compound of Preparation 29 (3.68 g, 23.1 mmol) was suspended in 60 ml toluene. Thionyl bromide (12.0 g, 57.8 mmol) was slowly added and the mixture was heated at 110°C for 1 h. The mixture was concentrated under reduced pressure and the residue was partitioned between water and dichloromethane. The aqueous phase was basified with potassium carbonate and extracted three times with dichloromethane. The combined organics were washed with water, brine and dried over sodium sulphate and evaporated. The residue was purified by column chromatography (ethyl acetate-hexane, 5:95) to give 3.5 g (15.8 mmol, 68percent) of the title compound as a solid. Purity 100percent.The title compound of Preparation 29 (3.68 g, 23.1 mmol) was suspended in 60 ml toluene. Thionyl bromide (12.0 g, 57.8 mmol) was slowly added and the mixture was heated at 110C for 1 h. The mixture was concentrated under reduced pressure and the residue was partitioned between water and dichloromethane. The aqueous phase was basified with potassium carbonate and extracted three times with dichloromethane. The combined organics were washed with water, brine and dried over sodium sulphate and evaporated. The residue was purified by column chromatography (ethyl acetate-hexane, 5:95) to give 3.5 g (15.8 mmol, 68percent) of the title compound as a solid. Purity 100percent. Step 1

Molecular Weight:222.08
XLogP3:2.8
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:220.98401
Monoisotopic Mass:220.98401
Topological Polar Surface Area:12.9
Heavy Atom Count:12
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes