N,N'-Dimethylethylenediamine → (1,1'-Biphenyl)-2-carbonitrile

Temperatur

110 °C

An oven dried screw cap test tube was charged with NaCN (93 mg, 1.898 mmol), dried KI (52 mg, 0.313 mmol, 20 mol %) and CuI (29 mg, 0.152 mmol, 10 mol %), evacuated and backfilled with argon three times. 2-Bromobiphenyl (270 μL, 1.566 mmol), N,N′-dimethylethylenediamine (170 μL, 1.597 mmol) and anhydrous toluene (1 mL) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 24 h. The resulting yellow suspension was cooled to room temperature, 2 mL of ethyl acetate, 1 mL of ammonium hydroxide (30%) and 1 mL of water were added. The mixture was stirred at 25° C. for 10 min, then the organic layer was separated and the aqueous layer was extracted three times with ethyl acetate (3×2 mL). The combined organic layers were washed with 5 mL of water and dried over MgSO4. The solvent was removed at reduced pressure. Purification of the residue by flash chromatography on silica gel (2×15 cm; hexane/ethyl acetate 10:1) provided 190 mg (68% yield) of the title compound as a colorless oil.

1. customAn oven dried screw
2. customcap test tube
3. customevacuated
4. customThe tube was sealed
5. temperatureThe resulting yellow suspension was cooled to room temperature
6. stirringThe mixture was stirred at 25° C. for 10 min
7. customthe organic layer was separated
8. extractionthe aqueous layer was extracted three times with ethyl acetate (3×2 mL)
9. washThe combined organic layers were washed with 5 mL of water
10. dry with materialdried over MgSO4
11. customThe solvent was removed at reduced pressure
12. customPurification of the residue by flash chromatography on silica gel (2×15 cm; hexane/ethyl acetate 10:1)

ORD-Eintrag

ord-9e2e2bfaf0e045b9981aa229be431852

Quelldatensatz

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06888032B2