Phenylboronic Acid → 4-bromo-1-(2,2-dimethylpropyl)-5-phenoxy-1H-benzotriazole

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Reaction Steps

4-Bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (1-6) (100 mg, 0.352 mmol, 1.0 equiv.), copper(II) acetate (63.9 mg, 0.352 mmol, 1.0 equiv.), phenylboronic acid (86 mg, 0.704 mmol, 2.0 equiv.) and freshly milled 4 Å molecular sieves were dried in vacuo and then suspended in anhydrous CH2Cl2 (3.5 mL) and TEA (245 μl, 1.760 mmol, 5.0 equiv.). The mixture was stirred ambient temperature for 18 hours, after which the mixture was filtered. The filtrate was concentrated in vacuo and the residue was purified via reverse phase HPLC (water/acetonitrile gradient containing 0.1% TFA) to provide 422. 1H NMR (CDCl3) δ 7.42 (1H, d, J=8.87 Hz), 7.36-7.30 (2H, m), 7.21 (1H, d, J=8.87 Hz), 7.12-7.07 (1H, m), 6.95 (2H, dd, J=7.97, 1.44 Hz), 4.40 (2H, s), 1.06 (9H, s) ppm. LRMS m/z (M+H) 360.0 and 362.0 (intensity ratio ˜1:1) found, 360.1 and 362.1 required.

Provenance & Evidence