Ethyl 4-bromobutyrate → Ethyl 4-(methylthio)butyrate

A solution of ethyl 4-bromobutyrate (0.26 g) in N,N-dimethylformamide (3 ml) was treated with sodium thiomethoxide (0.103 g), and the mixture stirred at room temperature overnight. The mixture was partitioned between water (10 ml) and dichloromethane (10 ml), and the organic layer was washed with 1:1 saturated aqueous sodium chloride and water (10 ml). The organic layers were evaporated in vacuo to give the title compound as a clear oil (0.135 g). NMR (CDCl3) 4.06δ(2H, q, CH2), 2.46δ(2H, t, CH2), 2.35δ(2H, t, CH2), 2.03δ(3H, s, CH3), 1.85δ(2H, m, CH2), 1.18δ(3H, t, CH3).

1. customThe mixture was partitioned between water (10 ml) and dichloromethane (10 ml)
2. washthe organic layer was washed with 1:1 saturated aqueous sodium chloride and water (10 ml)
3. customThe organic layers were evaporated in vacuo

ORD record

ord-caa573e0dbc74257968a0dd067fc32df

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07101882B2