杏耀测速代理_利用Sandmeyer反应由芳胺合成芳香磺酰氯

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Sandermeyer的另一个应用是直接得到芳香磺酰氯。这种反应对剂,反应条件的要求及控制都比成磺酸高。市场上有二氧化硫醋酸溶液出售。将芳胺做成重氮盐,以亚铜盐作为催化剂,醋酸做溶剂,再用二氧化硫处理就能够以较好的收率得到芳香磺酰氯。

杏耀测速代理_利用Sandmeyer反应由芳胺合成芳香磺酰氯

反应实例

To a suspension of4-amino--methyl-benzonitrile (500 mg, 3.00 mmol) in 1.8 mL of 6 N HClat room temperature was added 2 mL of water followed by a solution of NaNO2(220mg, 3.13 mmol) in 1 mL of water dropwise and the suspension stirred at roomtemperature for 20 min. The suspension was added to a solution of SO2inacetic (prepared by bubbling SO2 gas into acetic acid until saturation atroom temperature) and copper(II) dihydrate (60 mg, 3.52 mmol) in 0.15mL of water. The suspension was stirred at room temperature for 1.25 h andextracted with EtOAc. The organic layer was washed with water and brine, dried(MgSO4), filtered and concentrated under reduced pressure. Theresidue was purified by flash chromatography (silica gel, CH2Cl2/Hexanes,50:50, 75:25 and 100:0) to afford the title compound (305 mg) as a white solid.

【Markley, Lowell. D.; J.Med. Chem.; EN; 29; 3; 1986; 427-433】

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