1,2-Dimethoxyethane → 2-(4-Bromophenyl)thiophene-3-carbonitrile

Temperature

80 °C

A solution of 2-iodothiophene-3-carbonitrile (20 g, 85 mmol, preparation 23), 4 bromobenzeneboronic acid (18.8 g. 94 mmol), potassium carbonate (26 g, 187 mmol) and tetrakis(triphenylphosphine)-palladium (0) (10 g, 8.5 mmol) in a mixture of anhydrous dimethoxyethane (300 mL) and absolute ethanol (150 mL) is degassed with Ar or N2 for 15 min and stirred for 12 hours at 80° C. The reaction mixture is cooled to room temperature, water (100 ml) is then added and the crude product is extracted with methylene chloride (3×150 mL). The crude material is purified by column chromatography (hexane-ethyl acetate 10/1) to provide the title compound as a white solid. 1H NMR (CDCl3): 7.32 (m, 2H), 7.62 (m, 4H).

1. customis degassed with Ar or N2 for 15 min
2. temperatureThe reaction mixture is cooled to room temperature
3. additionwater (100 ml) is then added
4. extractionthe crude product is extracted with methylene chloride (3×150 mL)
5. customThe crude material is purified by column chromatography (hexane-ethyl acetate 10/1)

ORD record

ord-0f92c7ef215e4f239ddb7c25c4b440b8

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07625932B2