Boron tribromide → HCID 135524526, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-methoxy-3-(4-methoxy-2,5-dipropylphenyl)-1,2-benzisoxazole (193 mg, 0.57 mmol) in 1,2-dichloroethane (6.0 mL) at 0° C. was added BBr3 (5.7 mL, 5.7 mmol, 1.0 M in CH2Cl2) slowly. The resulting brown solution was stirred at 60° C. for 15 hr, cooled to 0° C., quenched carefully with water, and extracted in EtOAc (2×30 mL) with 2 N HCl (2×20 mL). Purification (twice) by flash chromatography with silica gel (gradient to 40% EtOAc/hexanes) furnished the title compound as a light yellow solid (163 mg, 93% yield): mp 162-163° C.; 1H NMR (300 MHz, acetone-d6) δ 0.80 (t, 3H, J=7.3 Hz), 0.97 (t, 3H, J=7.4 Hz), 1.52 (m, 2H), 1.67 (m, 2H), 2.65 (two overlapping triplets, 4H), 6.91 (s, 1H), 6.95 (dd, 1H, J=8.6, 2.0 Hz), 7.04 (d, 1H, J=1.8 Hz), 7.26 (s, 1H), 7.46 (d, 1H, J=8.6 Hz), 8.89 (broad s, 2H); MS m/e 312 (M+H)+.

Provenance & Evidence