Methyl vinyl ketone → 4-(2,4,6-Trichlorophenyl)but-3-en-2-one

Temperature

50 °C

A round bottom flask equipped with magnetic stirrer and nitrogen inlet was charged with but-3-en-2-one (1.14 g, 16.25 mmol), 1,3,5-trichloro-2-iodo-benzene (2.0 g, 6.5 mmol), Pd(OAc)2 (125 mg, 0.65 mmol), sodium hydrogen carbonate (1.64 g, 19.5 mmol) and tetrabutylammonium chloride (2.17 g, 7.8 mmol) in DMF (20 ml). The mixture was stirred at 50° C. for 24 hours. The reaction mixture was poured onto water (100 ml) and extracted with ether (3×50 ml). Combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography over silica gel (150 g) (eluent: n-hexane/ethyl acetate 1:20) to afford 1.02 g (63% of theory) of (E)-4-(2,4,6-trichloro-phenyl)-but-3-en-2-one in form of an oil.

1. customA round bottom flask equipped with magnetic stirrer and nitrogen inlet
2. additionThe reaction mixture was poured onto water (100 ml)
3. extractionextracted with ether (3×50 ml)
4. dry with materialCombined organic layers were dried over anhydrous sodium sulphate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash chromatography over silica gel (150 g) (eluent: n-hexane/ethyl acetate 1:20)

ORD record

ord-a8ef47bad49549b9bd169715089e0af6

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08357635B2