4-BROMO-7-CHLOROQUINOLINE

yellow powder

At 0 C under an atmosphere of argon, phosphorus tribromide (5.8 mL, 0.079 moles, 1.10 equiv.) was added slowly to a solution of 7-chloro-4-hydroxyquinoline (13.02 g, 0.073 moles, 1.00 equiv.) in anhydrous DMF (150 mL, 0.5 M soln.). The reaction was allowed to warm to rt and followed by TLC. Complete consumption of starting material was observed after 90 minutes stirring. The reaction mixture was poured onto ice and the pH was rendered alkaline using solid sodium bicarbonate. This resulted in a white precipitate. The mixture was then filtered and the resulting solid was dried under vacuum affording an off-white solid (17.30 g, 99 percent). The material was recrystallised from ethyl acetate to give white needles (12.20 g, 70percent). Rj-= 0.70 (hex:EtoAc; 1:1); Mp = 99— 101 °C, EtoAc (lit., Eur.J. Org. Chem. 20024181.103 — 104°C, hex).To a 20 mL microwave tube was added 4, 7-dichloroquinoline (0.3315 g, 1.674 mmol) and propionitrile (3 mL), followed by TMS-Br (0.434 mL, 3.35 mmol) at room temperature. A precipitate formed. The tube was sealed and heated to 100 °C for 12 h. The reaction was cooled to room temperature. The crude mixture was poured into ice-cooled NaOH (IN, 3 mL) and the tube was rinsed with water. The aqueous layer was extracted with diethyl ether (3x5 mL). The diethyl ether layer were combined, dried (Na2S04), filtered and concentrated under reduced pressure to give the 4-bromo-7-chloroquinoline (300 mg, 1.126 mmol, 67percent yield) as a yellow solid. NMR (400MHz, CHLOROFORM-d) δ 8.70 (d, J=4.6 Hz, IH), 8.17 (d, J=8.8 Hz, IH), 8.14 (d, J=2.0 Hz, IH), 7.73 (d, J=4.6 Hz, IH), 7.63 (dd, J=9.0, 2.0 Hz, IH); LCMS (ESI) m A mixture of tert-butyl (3-aminobicyclo[1.1.1]pentan-1-yl)carbamate (PharmaBlock, 800.0 mg, 4.04 mmol), A mixture of teri-butyl (3-aminobicyclo[l. l.l]pentan-l-yl)carbamate (PharmaBlock, 800.0 mg, 4.04 mrnol),

Molecular Weight:242.50
XLogP3:3.6
Hydrogen Bond Acceptor Count:1
Exact Mass:240.92939
Monoisotopic Mass:240.92939
Topological Polar Surface Area:12.9
Heavy Atom Count:12
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes