[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[CH:8]1[CH2:13][CH:6]([CH2:7]1)[C:5]2=O.CO.[NH2:17][OH:18].Cl.[OH-].[K+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]1[CH2:13][CH:6]([CH2:7]1)[C:5]2=[N:17][OH:18]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.
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