Water ethanol → HCID 67234001, compound

Participants

Reaction Steps

8-Bromo-2-(dibromomethyl)-6-fluoroquinoline (17.2 g, 43.2 mmol) was weighed into a flask and dissolved in 250 mL of EtOH, followed by addition of silver nitrate (23.5 g, 138 mmol) in 100 mL of 1:1 EtOH/H2O. The reaction was heated to reflux for 1 hour, at which time all starting material had been consumed. The reaction was removed from heat and filtered hot through a medium frit scintered glass funnel, affording 5.84 g of 8-bromo-6-fluoroquinoline-2-carboxylic acid as a white/yellow powder. The mother liquor was concentrated in vacuo, followed by extractive work-up (200 mL ethyl acetate/water). The combined organics were dried over Na2SO4 and concentrated in vacuo to afford the desired products as an orange-brown semi solid (99% overall; 6.4 g and 5.8 g respectively). MS APCI (+) m/z 298 and 300 (M+1 of each isotope) detected; MS APCI (−) m/z 268 and 269.9 (M−1 of each Br isotope) detected.

Provenance & Evidence