Cesium carbonate → (2,2-Diethoxyethyl)(2-fluorophenyl)sulfane

A mixture of 2-fluorothiophenol (1.00 g, 7.80 mmol), bromoacetaldehyde diethyl acetal (1.41 mL, 9.36 mmol), and Cs2CO3 (3.05 g, 9.36 mmol) in anhydrous DMF (20 mL) was stirred under N2 at room temperature overnight. The reaction mixture was filtered through a sintered funnel, and the filtrate was diluted with water (20 mL). The aqueous mixture was extracted with Et2O (3×100 mL), and the organic phase was dried over anhydrous MgSO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using a mixture of EtOAc and hexane as eluent to give (2,2-diethoxyethyl)(2-fluorophenyl)sulfane (1.81 g, 95%) as a viscous liquid. 1H NMR (400 MHz, CDCl3): δ 7.46-7.41 (m, 1H), 7.24-7.18 (m, 1H), 7.09-7.02 (m, 1H), 4.64 (t, 1H, J=5.6 Hz), 3.69-3.61 (m, 2H), 3.56-3.49 (m, 2H), 3.10 (d, 2 H, J=5.6 Hz), 1.17 (t, 6H, J=7.2 Hz).

1. filtrationThe reaction mixture was filtered through a sintered funnel
2. additionthe filtrate was diluted with water (20 mL)
3. extractionThe aqueous mixture was extracted with Et2O (3×100 mL)
4. dry with materialthe organic phase was dried over anhydrous MgSO4
5. filtrationfiltered
6. customevaporated to dryness under reduced pressure
7. customThe residue was purified by MPLC on silica gel using
8. additiona mixture of EtOAc and hexane as eluent

ORD record

ord-f0d721c4afcc4db1bdee4504d6921cf5

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080568B1