1,1-Dichloroethane → HCID 67171032, compound

Participants

Reaction Steps

To 4-(6-bromo-3,4-dihydronaphthalen-1-yl)morpholine (Preparation 20A, 0.36 g, 1.224 mmol) in dichloromethane (4 mL) was added N-hydroxy-4-propylbenzimidoyl chloride (Preparation 20B, 0.242 g, 1.224 mmol) dissolved in 1 mL of dichloromethane at room temperature. Next, triethylamine was added dropwise over a period of 5 min. at room temperature. The reaction mixture was stirred at room temperature for 14 h. and concentrated. The reaction mixture was partitioned between ethyl acetate (15 mL) and water (10 mL). The ethyl acetate layer was dried over sodium sulfate, filtered, and concentrated to yield an oil. To the oil was added dichloroethane (4.00 mL) followed by TFA (0.141 mL, 1.836 mmol) at room temperature. The reaction mixture was heated at 70° C. for 45 min., stirred at room temperature for 2 h, and partitioned between dichloromethane (10 mL) and sat. aq. sodium bicarbonate (10 mL). The dichloromethane layer was dried over sodium sulfate, concentrated, and purified by silica gel column chromatography employing hexane/ethyl acetate. The desired fractions were collected and concentrated to yield 7-bromo-3-(4-propylphenyl)-4,5-dihydronaphtho[2,1-d]isoxazole (0.32 g, 0.869 mmol, 71.0% yield) as a white solid. LCMS M+1=369.

Provenance & Evidence