3'-Bromoacetophenone → 1-(3-Sulfanylphenyl)ethan-1-one

Participants

Reaction Conditions

Reaction Steps

A solution of 3′-bromoacetophenone (10 g, 50 mmol), N,N-diisopropylethylamine (18 mL, 0.10 mol), 3-mercaptopropionic acid 2-ethylhexyl ester (11 mL, 48 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.29 g, 0.50 mmol) and tris(dibenzylideneacetone)palladium(0) (0.46 g, 0.50 mmol) in 1,4-dioxane (250 mL) was stirred at 100° C. for 2 days. After the reaction solution was filtered with celite, the filtrate was concentrated in vacuo until the volume became one third approximately. Water (200 mL) was added thereto, extracted with ethyl acetate (200 mL). The organic layer was washed with brine (200 mL) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give a mixture including 3-(3-acetylphenyl)thiopropionic acid 2-ethylhexyl ester (19 g). This mixture (17 g) was dissolved in tetrahydrofuran (200 mL), sodium ethoxide (7.0 g, 0.10 mol) in ethanol (40 mL) was added thereto, and then the whole was stirred at 50° C. for 2 hours. Water (200 mL) was added to the reaction solution and washed with ethyl acetate (200 mL). 1N Hydrochloric acid (100 mL) was added to the aqueous layer and extracted with ethyl acetate (300 mL), then the organic layer was washed with brine (100 mL) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title reference compound (6.2 g) as a brown oil (Yield 81%).

Provenance & Evidence