Water → 2-(4-Methanesulfonamidophenoxy)ethyl bromide

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Reaction Steps

2-(4-nitrophenoxy)ethyl bromide (0.5 g, 2.03 mmol) was dissolved in methanol (30 ml) and, after adding 10% Pd/C (0.2 g), the solution was stirred for 1 h in hydrogen gas, followed by filtration. The filtrate was concentrated under vacuum and the residue was dissolved in pyridine (20 ml). To the resulting solution, methanesulfonyl chloride (0.25 ml, 3.2 mmol) was slowly added dropwise, followed by stirring overnight. Water was poured into the reaction mixture, followed by extraction with ethyl acetate and concentration under vacuum. The residue was subjected to column chromatography using a 1:1 solvent system of ethyl acetate and hexane as an eluent to yield the end compound 2-(4-methanesulfonamidophenoxy)ethyl bromide (0.22 g).

Provenance & Evidence