1-Bromo-2-chloro-4-fluorobenzene → (4-Bromo-3-chlorophenyl)(ethyl)sulfane

Temperature

100 °C

To a room temperature solution of 1-bromo-4-fluoro-2-chlorobenzene (1.9 g, 0.97 mmol) in DMSO (10 mL) was added sodium ethanethiolate (0.84 g, 1 mmol) and the resulting reaction mixture was heated to 100° C. for 18 hours. The reaction mixture was partitioned between water (20 mL) and EtOAc (50 mL). The organic layer was separated and the aqueous layer was further extracted with EtOAc (3×50 mL). The organic layers were combined and washed with saturated brine solution (20 mL) then dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography eluting with heptane to afford the title compound as a colourless liquid in 70% yield, 1.6 g.

1. customthe resulting reaction mixture
2. customThe reaction mixture was partitioned between water (20 mL) and EtOAc (50 mL)
3. customThe organic layer was separated
4. extractionthe aqueous layer was further extracted with EtOAc (3×50 mL)
5. washwashed with saturated brine solution (20 mL)
6. dry with materialthen dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude material was purified by silica gel column chromatography
10. washeluting with heptane

ORD record

ord-58a825bc282a4f378ff31070491cae93

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952008B2