2,3-Dichlorophenol → 2-(3,4-Dichlorophenoxy)ethanamine

Participants

Reaction Steps

A solution of 1.0 g of (2-hydroxy-ethyl)-carbamic acid tert-butyl ester, 0.96 g of 2,3-dichlorophenol, and 1.54 g of triphenylphosphine in THF (20 mL) was stirred as 1.19 g of diisopropyl azodicarboxylate was added. After stirring at ambient temperature for 72 h, the solvent was removed and the residue was dissolved in 10% sulfuric acid (10 mL) and warmed to 80° C. After 16 h, the reaction was cooled to ambient temperature and the mixture diluted with water and washed with EtOAc (2×). The organic layers were washed with water, and the pH of the combined aqueous layers was adjusted to 9 with 10 N NaOH solution. The mixture was extracted with chloroform (3×) and the combined organic layers were washed with sat. sodium chloride solution, dried over sodium sulfate, filtered and concentrated to provide the title compound as an orange oil. MS (M+H−)=204.2.

Provenance & Evidence