Potassium Cyanide → HCID 18537140, compound

To a solution of 3.82 g (17.3 mmol) methyl 4-bromothiophene-2-carboxylate (as prepared in the previous step) in 10 mL of anhyd DMF was added 3.10 g (34.6 mmol) of copper (I) cyanide. The mixture was heated to reflux with stirring for 18 h, cooled and poured into 100 mL of 10% (w/v) KCN. The mixture was extracted with EtOAc (3×60 mL) and the combined extracts were washed with 150 mL each of water and brine. The dark solution was dried over Na2SO4, treated with decolorizing carbon, filtered and the resulting colorless solution concentrated in vacuo. The resulting light yellow solid was recrystallized from MeOH to afford the title compound as a cream-colored solid (1.67 g, 58%). 1H-NMR (300 MHz, CDCl3) δ8.09 (d, 1H, J=1.4 Hz), 7.93 (d, 1H, J=1.4 Hz), and 3.93 (s, 3H). IR (film): 2235 and 1712 cm−1.

1. temperatureThe mixture was heated
2. temperatureto reflux
3. temperaturecooled
4. extractionThe mixture was extracted with EtOAc (3×60 mL)
5. washthe combined extracts were washed with 150 mL each of water and brine
6. dry with materialThe dark solution was dried over Na2SO4
7. additiontreated with decolorizing carbon
8. filtrationfiltered
9. concentrationthe resulting colorless solution concentrated in vacuo
10. customThe resulting light yellow solid was recrystallized from MeOH

ORD record

ord-338fa181fd854b638298bfdaab59024a

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06492403B1