Propanoic acid, 2-bromo-2-methyl-, ethyl ester → 2-Methyl-2-(4-trifluoromethyl-phenylsulfanyl)-propionic acid ethyl ester

To a stirred solution of 10 g (56 mmol) of 4-trifluoromethylbenzene-1-thiol in ethanol (100 mL) were added 3.14 g (56 mmol) KOH pellets, followed by 10.95 g (56 mmol) ethyl α-bromoisobutyrate. The reaction mixture was heated to reflux for 18 h. The reaction was cooled to room temperature. The solid (KBr) was separated by filtration and rinsed with ethanol (20 mL). The filtrate was concentrated under reduced pressure and the residue dissolved in DCM (60 mL). The organic layer was washed with water (2×30 mL). The aqueous washes were back-extracted with DCM (15 mL). The combined organics were washed with brine and dried over Na2SO4. Filtration and concentration under reduced pressure afforded 16.3 g of 2-methyl-2-(4-trifluoromethyl-phenylsulfanyl)-propionic acid ethyl ester.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 18 h
3. customThe solid (KBr) was separated by filtration
4. washrinsed with ethanol (20 mL)
5. concentrationThe filtrate was concentrated under reduced pressure
6. dissolutionthe residue dissolved in DCM (60 mL)
7. washThe organic layer was washed with water (2×30 mL)
8. extractionThe aqueous washes were back-extracted with DCM (15 mL)
9. washThe combined organics were washed with brine
10. dry with materialdried over Na2SO4
11. filtrationFiltration and concentration under reduced pressure

ORD record

ord-d30ed9ffba944c16aec77721e5ad5014

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299111B2