Ethyl bromoacetate → Acetic acid, (phenylthio)-, ethyl ester

Participants

Reaction Steps

10.8 g (0.098 mol) of benzenethiol in 70 mL of DMF at 0° C., were treated with 4.31 g (0.108 mol, 1.1 eq) of NaH (55% in oil) over 40 min. 17.19 g (0.103 mol, 1.05 eq) of bromo-acetic acid ethyl ester were added, and stirring was continued over night. The reaction mixture was partitioned between aqueous NH4Cl and EtOAc, dried over Na2SO4, filtered and evaporated, to afford 15.4 g (80%) of phenylsulfanyl-acetic acid ethyl ester as a colorless oil, MS: 197 (MH+).

Provenance & Evidence