Methanol → HCID 86693063, compound

Participants

Reaction Conditions

Reaction Steps

Into a 20-L 4-necked round-bottom flask was placed 6-Bromo-7-fluoro-2,3-dihydro-1H-1,3-methano-naphthalen-4-one (920 g, 3.88 mol, 1.00 equiv), methanol (7.5 L), tetrahydrofuran (2.5 L), NH2OH.HCl (538.2 g, 2.00 equiv), and KOH (655.2 g, 3.00 equiv, 50%). The resulting solution was stirred at 80° C. for 2.5 h and cooled to 25° C. The solids were filtered out and washed with 3×1 L of DCM. The filtrate was concentrated under vacuum and the residue was diluted with 5 L of H2O and 8 L of EA. The pH value of the solution was adjusted to 7 with HCl (3 M). The organic layer was washed with 1×2 L of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 980 g (crude) of 6-Bromo-2,3-dihydro-1H-1,3-methano-naphthalen-4-one oxime as a dark red solid.

Provenance & Evidence