1,3-Dibromopropane → 4-(3-Bromo-propoxy)-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester

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Reaction Steps

This compound was produced using similar methods as those used in Step 4, example 27, starting with 4-hydroxy-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester (1.49 g, 4.19 mmol), 1,3-dibromopropane (3.39 g, 16.8 mmol) and potassium carbonate (2.90 g, 21.0 mmol) in acetone (85 mL). The crude oil was purified by flash chromatography through silica gel using ethyl acetate/hexanes (0/100 gradient to 12/88) to give 4-(3-bromo-propoxy)-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester (1.49 g, 75%) as a white powder. 1H NMR (400 MHz, CDCl3); δ 12.30 (s, 1H), 8.57 (d, 1H), 8.10 (d, 2H), 8.02 (d, 1H), 7.36 (d, 2H), 6.65 (dd, 1H), 4.24 (t, 2H), 3.93 (s, 3H), 3.61 (t, 2H), 2.35 (m, 2H).

Provenance & Evidence