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With hydrogenchloride; magnesium; In water; benzene;
3',5'-Dichloroacetophenone To a suspension of magnesium turnings (2 g.) in dry ether (20 ml.), under nitrogen was added iodomethane (12 g.), in dry ether (50 ml.), at such a rate that the reaction refluxed. The addition took 1 hour. Dry benzene (150 ml.) was added and the ether blown off under a strong stream of nitrogen. 3,5-Dichlorobenzonitrile (5 g.) was dissolved in dry benzene (60 ml.) and then added dropwise over 10 minutes and the resulting mixture refluxed for 3 hrs. After cooling to 0 6N hydrochloric acid (100 ml.), was added slowly over 10 minutes. The resulting mixture was refluxed for 6 hours. After cooling water (50 ml.) and ether (50 ml.) were added and the mixture filtered. The aqueous phase was washed with ether (2*50 ml.), and the combined organic layers washed with sodium hydrogen carbonate solution (50 ml.), brine (50 ml.) and dried over magnesium sulphate. Evaporation yielded the title compound. Nuclear Magnetic Resonance spectrum (NMR) was as follows: 2.6, 3H, s; 7.4, 1H, m; 7.6, 2H, d.
A solution of methyl iodide (4 mL) in anhydrous Et20 (40 mL) was dropped into a suspension of magnesium (1.6 g) in anhydrous [ET20] (16 mL) under a Nitrogen atmosphere. At the end of the dropping, benzene (120 mL) was added and the [ET20] eliminated with a Nitrogen flux. Then, a solution of 3, 5-dichlorobenzonitrile (4 g) in benzene (48 mL) was added and the mixture was heated to reflux for 3 hours. The solution was cooled to [0C] and a 6N hydrochloric acid solution was added and the mixture was stirred overnight at r. t.. Water and [ET20] were added and the layers were separated. The organic phase was washed with a saturated sodium hydrogen carbonate solution and brine, dried and concentrated in vacuo. The residue was purified by flash chromatography (CH/AcOEt 95: 5) to give the title compound (2.55 g) as an orange oil. T. [I.] c.: CH/AcOEt 8: 2, Rf=0.64. NMR [(CDCI3)] : 8 (ppm) 7.75 (s, 2H); 7.6 (s, [1 H)] ; 2.55 (s, 3H).
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