4-Bromo-1,1,1-trifluorobutane → 2-Methyl-2-(4,4,4-trifluoro-butylsulfanyl)-propionic acid ethyl ester

Temperature

85 °C

To a solution of 149 g (0.785 mol) of 2-acetylsulfanyl-2-methyl-propionic acid ethyl ester (prepared as described in Method C, step 1) in ethanol (1.2 L, degassed under nitrogen for 1 h) are added 169.7 g (0.105 mol) of sodium methoxide, followed by a solution of 150 g (0.785 mol) of 4-bromo-1,1,1-trifluoro-butane. The reaction is heated to 85° C. for 3 d. The solvent is removed under reduced pressure. The residue is dissolved in DCM (1 L) and washed with saturated aqueous NaHCO3 solution (2×1 L). The organic layer is dried over Na2SO4, filtered and the filtrate is concentrated under reduced pressure to afford 171 g of 2-methyl-2-(4,4,4-trifluoro-butylsulfanyl)-propionic acid ethyl ester as a brown oil. Yield: 84%; ES-MS: m/z 259 [M+H]; 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.29 (3H, t, J=7.17 Hz), 1.51 (6H, s), 1.76-1.86 (2H, m), 2.12-2.27 (2H, m), 2.69 (2H, t, J=7.17 Hz), 4.18 (2H, q, J=7.17 Hz)

1. customThe solvent is removed under reduced pressure
2. dissolutionThe residue is dissolved in DCM (1 L)
3. washwashed with saturated aqueous NaHCO3 solution (2×1 L)
4. dry with materialThe organic layer is dried over Na2SO4
5. filtrationfiltered
6. concentrationthe filtrate is concentrated under reduced pressure

ORD record

ord-bcccf2d2a2c6433b88707382902f96c7

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372874B2