Ethyl Acetate → 4-(4-Amino-2,6-dimethylphenoxy)-2-(4-fluorobenzenesulfonyl)phenol

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Reaction Steps

To a solution of 4-(2,6-dimethyl-4-nitro-phenoxy)-2-(4-fluoro-benzenesulfonyl)-phenol (11.4 grams, 27.4 mmol) in a mixture of ethanol (200 mL and ethyl acetate (200 mL) was added catalyst (10% palladium on carbon, 2.3 grams). The mixture was hydrogenated under 45 psi at room temperature for 4 hours. The mixture was filtered through Celite and concentrated to give the title compound of Step D (10.5 grams) as a tan solid. The product was used in the next step without further purification. 1H NMR (400 MHz, CD3OD) δ7.98-7.92 (m, 2H), 7.29-7.22 (m, 2H), 7.21 (d, 1H), 6.92 (dd, 1H), 6.78 (d, 1H), 1.98 (s, 6H). MS (APCI−) Calc.:387.1, Found: 386.2 (M−1).

Provenance & Evidence