4-Bromobenzoyl chloride → 1-(4-Bromophenyl)-2-(3-fluoro-4-methylthiophenyl)ethanone

To the mixture of 4-bromobenzoyl chloride (10.81 g, 49.26 mmol), zinc (4,40 g, 67.24 mmol) and tetrakis(triphenylphosphine)palladium(0) (2.99 g, 2.586 mmol) in DME (250 mL) was added dropwise the solution of 4-(bromomethyl)-2-fluoro-1-(methylsulfanyl)benzene (12.16 g, 51.72 mmol) in DME (120 mL) at room temperature. After 2.5 hour, the mixture was filtered through celite, the filtrate was evaporated, diluted with ethyl acetate (300 mL), washed with water (100 mL), brine (100 mL), dried over sodium sulfate, and concentrated in vacuo. The residue was washed with ethyl acetate-isopropylether, to give the subtitle compound (12.16 g, 73% yield) as a solid.

1. filtrationthe mixture was filtered through celite
2. customthe filtrate was evaporated
3. additiondiluted with ethyl acetate (300 mL)
4. washwashed with water (100 mL), brine (100 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. washThe residue was washed with ethyl acetate-isopropylether

ORD record

ord-eaba5431c1e243d1aab548f7b379e082

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06608095B2