Isoxazole, 4-(chloromethyl)-3,5-dimethyl- → 4-[(3,5-Dimethyl-4-isoxazolyl)methoxy]-2,6-difluorobenzenemethanol

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Reaction Steps

PS-BEMP (1.5 g, 2 eq) was added to a solution of 2,6-difluoro-4-hydroxybenzyl alcohol (400 mg, 1.5 eq) in acetonitrile (4 mL) and the mixture was shaken for 5 min. 4-(Chloromethyl)-3,5-dimethylisoxazole (210 uL, 1.67 mmol) was added and the resultant mixture was shaken at ambient temperature for 16 h. The mixture was filtered, the resin washed with dichloromethane (4×4 mL) and evaporated to afford the desired product (380 mg, 85%) as a white solid: NMR δH(400 MHz; d6-DMSO) 2.20 (3H, s), 2.40 (3H, s), 4.42 (2H, d, J 5.5 Hz), 5.95 (2H, s), 5.08 (1H, t, J 5.5 Hz) and 6.76–6.83 (2H, m); HPLC (XTERRA, 50/80, 220 nm) 94.5% (1.03 min).

Provenance & Evidence