tert-Butyl bromoacetate → (4-Hydroxy-2-methyl-phenylsulfanyl)-acetic acid tert-butyl ester

Participants

Reaction Steps

A solution of 10 g (71 mmol) of 4-mercapto-3-methyl-phenol (DE 2101359) and 10.5 ml (1 eq., 71 mmol) of bromo-acetic acid tert-butyl ester in 250 ml of THF was treated at room temperature with 12.2 ml (1 eq., 71 mmol) of N-ethyldiisopropylamine. The suspension was heated at reflux for 1 h, cooled to ambient temperature, and treated with water. The reaction mixture was then poured onto 0.1 M HCl/AcOEt, the organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. Purification by flash chromatography (SiO2, heptane/toluene/AcOEt=10/1/1) afforded finally 5.6 g of the title product as white solid.

Provenance & Evidence