Water → HCID 135627611, compound

Participants

Reaction Steps

Anhydrous ferric chloride (53.5 g, 0.33 mol) was added over a period of 180 minutes to a solution of 2-(2H-benzotriazol-2-yl)phenol, (20.0 g, 94.7 mmol), prepared by the method of Rosevear and Wilshire (Scheme I), Aust. J. Chem. 1985, 38, 1163-76, in methylene chloride (200 mL) and water (160 mg) at 0° C. After the addition was complete, the resulting mixture was removed from the cooling bath and stirred at room temperature for 36 hours. HPLC analysis of the reaction mixture (detector wavelength=290 nm) indicated 87 area % of product and 13 area % of starting material. The mixture was diluted with 2 L of methylene chloride and extracted with two 500 mL portions of 5% HCl, and two 1 L portions of water. The organic layer was rotary evaporated, leaving 19.4 g of a light grey solid which was 90% pure to HPLC. Surprisingly, very little or none of the para coupled product was found, as confirmed by NMR analysis. Recrystallization from o-dichlorobenzene gave COMPOUND 5 as off-white needles. 1H NMR (300 MHz, CD2Cl2) δ 11.62 (s, 2H), 8.41 (d, 2H), 7.88 (m, 4H), 7.42 (m, 4H), 7.39 (m, 2H), 7.10 (t, 2H).

Provenance & Evidence