Nitrogen → 2-(4-Bromophenyl)thiophene-3-carbonitrile

Temperature

80 °C

Degass a solution of 2-iodo-thiophene-3-carbonitrile (20 g, 85 mmol), 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) with Ar or N2 for 15 min and stir for 12 hours at 80° C. Cool the reaction mixture to room temperature, add water (100 ml) and extract the crude product dichloromethane (3×150 mL). Purification by chromatography (hexane-ethyl acetate 10/1) yields 16.3 g (72%) as a white solid: 1H NMR (CDCl3): δ 7.32 (m, 2H), 7.62 (m, 4H).

1. temperatureCool the reaction mixture to room temperature
2. extractionextract the crude product dichloromethane (3×150 mL)
3. customPurification by chromatography (hexane-ethyl acetate 10/1)
4. customyields 16.3 g (72%) as a white solid

ORD record

ord-3836629298ae4afa8cc807ef58348857

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07642361B2