3 91 m 2h 2 11 br s 2h a solution of 3 4 bromo 2 chlorophenoxy propane 1 2 diol 1 0 g 3 7 mmol in dmf 20 ml was added copper i cyanide 365 mg 4 1 mmol after submitting to microwave induction at 150 u00b0 c for 2 h the reaction mixture was cooled to rt and diluted with water extraction with ethyl acetate washed with brine dried over magnesium sulfate and concentrated the crude material was purified by mplc 5 ethyl acetate in hexanes to give rise to 370 mg of intermediate 2 1 h nmr cdcl 3 u03b4 7 67 d j 2 1 hz 1h 7 56 dd j 8 5 2 1 hz 1h 7 01 d j 8 5 hz 1h 4 16 4 22 m 3h 3 81 3 91 m 2h 2 35 br s 2h to a solution of 3 chloro 4 2 3 dihydroxypropoxy benzonitrile 1 11 g 4 9 mmol in methanol 10 ml at 50 u00b0 c was added hydroxylamine solution 50 wt in water 0 9 ml after stirring at 50 u00b0 c for 6 h the reaction mixture was cooled to rt and concentrated purification by mplc 10 ethyl acetate in hexanes gave 1 5 g of intermediate 3 as a colorless solid 1 h nmr cd 3 od u03b4 7 67 d j 2 1 hz 1h 7 54 dd j 8 6 2 2 hz 1h 7 10 d j 8 5 hz 1h 3 97 4 17 m 3h.