1-Naphthalenecarboxaldehyde, 4-bromo-, oxime → HCID 118046649, compound

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Reaction Steps

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed dichloromethane (100 mL), (E)-N-[(4-bromonaphthalen-1-yl)methylidene]hydroxylamine (4.5 g, 17.99 mmol, 1.00 equiv), 1-chloro-3-(trifluoromethyl)-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (4.9 g, 17.84 mmol, 1.00 equiv), chlorosylsodium (30 mL). The resulting solution was stirred overnight at room temperature. The aqueous layer was extracted with 3×20 mL of dichloromethane and the organic layers combined and washed with 3×40 mL of brine. The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and washed with ethyl acetate/petroleum ether (1/10-1/5). This resulted in 7.1 g (75%) of 3-(4-bromonaphthalen-1-yl)-5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole as a off-white solid.

Provenance & Evidence