Bromine → HCID 71743938, compound

Participants

Reaction Steps

To a solution of 8-Methylquinazoline (10 g, 0.0694 mol) in conc.H2SO4 (100 mL), was added silver sulphate (34.64 g, 0.1111 mol) in portions at OCC. To this was added Bromine (4.4 mL, 0.0832 mol) in drops. The reaction mixture was stirred at RT for 16 h. Reaction was monitored by LCMS at regular intervals. At the end of 16 h, LCMS showed 42% starting material and 51% of product. The reaction mixture was quenched with ice and basified with NH4OH solution. The aqueous layer was extracted with EtOAc (4×500 mL), washed with water and brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum. The crude was purified by column chromatography using neutralized silica gel (60-120 mesh) and pet ether/ethyl acetate as an elutent to yield the titled compound as pale yellow liquid (51% yield). 1H NMR (DMSO-d6, 400 MHz) δ 9.60-9.58 (s, 1H), 9.40-9.38 (s, 1H), 7.93-7.91 (d, J=7.72 Hz, 1H), 7.77-7.75 (d, J=7.72 Hz, 1H), 2.62 (s, 3H).

Provenance & Evidence