Diethylamine → HCID 57548582, compound

Temperature

90 °C

To a pressure vessel purged with N2 was added 3,4-dibromo-selenophene (3.69 g, 12.77 mmol), DMF (10.0 mL), triphenylphosphine (0.669 g, 2.55 mmol), copper(I) iodide (0.161 g, 0.843 mmol), diethylamine (dried over KOH, 20.0 mL, 191.55 mmol), (trimethylsilyl)acetylene (0.910 mL, 6.39 mmol), and palladium dichloride-bis-triphenylphosphine (0.592 g, 0.843 mmol). The reaction vessel was sealed and the mixture heated to 90° C. for 1 h. Upon cooling to room temperature, the reaction mixture was diluted with MTBE (100.0 mL) and was washed with 0.1 M HCl (3×50.0 mL). The combined aqueous layers were extracted with MTBE (50.0 mL). The combined MTBE extracts were quenched with saturated sodium bicarbonate (50.0 mL), dried over magnesium sulfate, and concentrated to an oil. The crude oil was purified by column chromatography (silica gel, cyclohexane) to provide (4-bromo-selenophen-3-ylethynyl)-trimethyl-silane (1.55 g, 5.08 mmol, 79.5 mol %): 500 MHz 1H NMR (CDCl3) δ 8.15 (d, J=2.9 Hz, 1H), 7.58 (d, J=2.9 Hz, 1H), 0.26 (S, 9h); 125 MHz 13C NMR (CDCl3) δ 135.4, 127.0, 126.4, 114.1, 99.8, 96.8, 0.2.

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 (3×50.0 mL)
5. extractionThe combined aqueous layers were extracted with MTBE (50.0 mL)
6. customThe combined MTBE extracts were quenched with saturated sodium bicarbonate (50.0 mL)
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated to an oil
9. customThe crude oil was purified by column chromatography (silica gel, cyclohexane)

ORD record

ord-b17be20c8e114b57b800ad667b572127

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148548B2