Cesium carbonate → 1-Bromo-4-(2-chlorophenylsulfanyl)-benzene

Temperature

130 °C

N-Methyl-2-pyrrolidone (10 mL) was added to 4-bromothiophenol (0.500 g, 2.64 mmol) in a sealed tube and the mixture was purged with argon for 5 minutes. To this mixture was added 2-chloro-iodobenzene (0.63 g, 2.64 mmol). Copper(I) chloride (0.131 g, 1.32 mmol), tetramethyl heptanedione (0.14 mL, 0.66 mmol) and cesium carbonate (1.70 g, 5.22 mmol) were added. The reaction mixture was stirred at 130° C. under argon for 2 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through a celite bed. The filtrate was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield the crude product. Silica gel chromatography (neat hexanes) provided impure 1-bromo-4-(2-chlorophenylsulfanyl)-benzene (0.44 g). MS calcd. for C12H8BrS [(M−Cl)] 265, obsd. 265.

1. customthe mixture was purged with argon for 5 minutes
2. temperatureThe reaction mixture was cooled to room temperature
3. filtrationfiltered through a celite bed
4. washThe filtrate was washed with water and brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customto yield the crude product

ORD record

ord-d202b246e3fd4eb3bcc166d630b4ca81

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000044B2