4-Bromobenzophenone → phenyl-[4-(phenylethynyl)phenyl]methanone

In argon atmosphere, 0.15 M Solution of tri-tert-butylphosphine in cyclohexane (12.0 mL, 18.0 mmol) was added to a stirred suspension of copper(I) iodide (350 mg, 1.8 mmol) and dichloro(bisbenzonitrile)palladium (350 mg, 0.9 mmol) in tetrahydrofuran (100 mL) at ambient temperature. The mixture was stirred for 5 min, N,N-diisopropylamine (4.5 mL, 30 mmol) was added, the mixture was stirred for next 5 min and then a solution of 4-bromobenzophenone (3.92 g, 15 mmol) and phenylacetylene (2.30 g, 22.5 mmol) in tetrahydrofuran (20 mL) was added dropwise during 15 min. The reaction mixture was stirred at ambient temperature overnight and then diluted with benzene (200 mL). The benzene solution was washed with water (2×80 mL) and 1.5 M aqueous solution of tartaric acid (30 mL); the organic solution was dried with anhydrous magnesium sulfate and subsequently evaporated in vacuo. The residue was purified by column chromatography (silica gel Fluka 60, hexane/ethyl acetate 95:5) yielding phenyl-[4-(phenylethynyl)phenyl]methanone.

1. stirringthe mixture was stirred for next 5 min
2. stirringThe reaction mixture was stirred at ambient temperature overnight
3. washThe benzene solution was washed with water (2×80 mL) and 1.5 M aqueous solution of tartaric acid (30 mL)
4. dry with materialthe organic solution was dried with anhydrous magnesium sulfate
5. customsubsequently evaporated in vacuo
6. customThe residue was purified by column chromatography (silica gel Fluka 60, hexane/ethyl acetate 95:5)

ORD record

ord-19ac024737fd4c67b520d8b194b0c16f

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08551993B2