Thionyl Chloride → 4-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazole

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Reaction Steps

Thionyl chloride (87 mL, 1.20 mol) was added dropwise to a stirred solution of benzotriazole (143 g, 1.20 mol) in dichloromethane (400 mL) at room temperature. The resulting solution was added dropwise during 30 min to a stirred solution of [3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methanol (263 g, 0.92 mol) in dichloromethane (700 mL). A very mild exothermic reaction occurred with precipitation of benzotriazole hydrochloride. The mixture was filtered to remove the benzotriazole hydrochloride. The filtrate was washed with water (2×800 mL), 1N sodium hydroxide (800 mL) and then dried over anhydrous sodium sulfate. The resulting solution was filtered and concentrated to give 288 g of the product as a pale yellow oil. 1H NMR (DMSO-d6): δ 7.66 (m, 2H), 7.61-7.57 (m, 1H), 4.47 (s, 2H), 3.45 (septet, J=7 Hz, 1H), 1.31 (d, J=7 Hz, 6H). ESI-LCMS m/z 279 (M+H)+.

Provenance & Evidence