Diethylamine → HCID 57548577, compound

Temperature

70 °C

To a pressure vessel purged with N2 was added 3-bromo-4-iodo-selenophene (1.97 g, 5.87 mmol), DMF (5.20 mL), triphenylphosphine (0.307 g, 1.17 mmol), copper(I) iodide (0.0740 g, 0.387 mmol), diethylamine (dried over KOH, 9.20 mL, 88.0 mmol), phenyl acetylene (0.645 mL, 5.87 mmol), and palladium dichloride-bis-triphenylphosphine (0.272 g, 0.387 mmol). The reaction vessel was sealed and the mixture heated to 70° C. for 1 h. Upon cooling to room temperature, the reaction mixture was diluted with MTBE (50.0 mL) and was washed with 0.1 M HCl (3×30.0 mL). The combined aqueous layers were extracted with MTBE (30.0 mL). The MTBE rich layer was dried over magnesium sulfate and concentrated to an oil. The crude oil was purified by column chromatography (silica gel, cyclohexane) to provide 3-bromo-4-phenylethynyl-selenophene (1.07 g, 3.19 mmol, 54.3 mol %): 500 MHz 1H NMR (CDCl3) δ 8.18 (d, J=2.9 Hz, 1H), 7.90 (d, J=2.9 Hz, 1H), 7.58-7.54 (m, 2H), 7.36-7.32 (m, 3H); 125 MHz 13C NMR (CDCl3) δ 134.2, 131.7, 128.5, 128.4, 126.8, 126.3, 122.9, 114.1, 91.0, 84.7.

1. customTo a pressure vessel purged with N2
2. customThe reaction vessel was sealed
3. temperatureUpon cooling to room temperature
4. washwas washed with 0.1 M HCl (3×30.0 mL)
5. extractionThe combined aqueous layers were extracted with MTBE (30.0 mL)
6. dry with materialThe MTBE rich layer was dried over magnesium sulfate
7. concentrationconcentrated to an oil
8. customThe crude oil was purified by column chromatography (silica gel, cyclohexane)

ORD record

ord-0441c1722a2a434aaa28f603a4fbe4d4

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148548B2