Triethylamine → 5-(3,5-Dichloro-phenyl)-3-(4-fluoro-naphthalen-1-yl)-5-trifluoromethyl-4,5-dihydro-isoxazole

Participants

Reaction Conditions

Reaction Steps

N-chlorosuccinimid (4.7 g) is added to a solution of 4-fluoro-naphthalene-1-carbaldehyde oxime (6.6 g, example 5 step A) in DMF (50 ml). After 45 minutes at 40° C., the reaction is cooled down to 0° C. and 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene, (8.4 g, example 1 step A) and triethylamine (5.4 ml) are added. The reaction is then further reacted at room temperature for 3 hours. Water is added (50 ml) and the reaction mixture is extracted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo. The crude product is dissolved in dichloromethane and filtered over a pad of silica gel to yield 5-(3,5-dichloro-phenyl)-3-(4-fluoro-naphthalen-1-yl)-5-trifluoromethyl-4,5-dihydro-isoxazole as a beige solid.

Provenance & Evidence