Diethyl Ether → 4-(2-Aminoethyl)-2-chlorophenol

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Reaction Steps

0.1 mol of 2-(4-Methoxy-phenyl)-ethylamine was dissolved in 200 ml of acetic acid, followed by addition of 1.5 eq. of sulfuryl chloride at 0° to 5° C. The solution was stirred at room temperature for 1 hour. 250 ml of ether was added and the resulted solid was collected by filtration. The solid was heated in 48% aqueous HBr at 135° C. for 4 hours, cooled to 0° C., and the crystal was collected by filtration and washed with small amount of methanol then with ethyl acetate. LC-MS showed the product as HBr salt had the expected M+H+ of 186. 1H NMR (Varian 300 MHz, CD3OD shifts relative to the solvent peak at 3.3 ppm) δ 7.2 (d, 1H) 7.0 (m, 1H) 6.9 (d, 1H) 3.1 (m, 2H) 2.9 (m, 2H).

Provenance & Evidence