Methyl iodide → 2-(5-Bromo-2-naphthalenyl)propionitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of LDA [lithium diisopropylamine prepared from diisopropylamine (1.49 g, 14.8 mmol) and n-BuLi (9.25 mL, 14.8 mmol, 1.6M solution in hexanes)]in THF (80 mL) at -78° C. was added (5-bromo-2-naphthalenyl) acetonitrile (3.80 g, 13.4 mmol) in THF (70 mL) dropwise over 45 minutes. The resulting orange solution was stirred at -78° C. for 10 minutes and MeI (1.90 g, 13.4 mmol) was added in one portion. The reaction mixture was stirred at -78° C. for 1 hour and quenched with saturated NH4Cl (20 mL). The solution was warmed to room temperature and the volatiles removed in vacuo. The residue was diluted with H2O (100 mL) and extracted with Et2O (3×150 mL). The combined organic layers were dried (MgSO)4) and concentrated in vacuo to give the crude product as a yellow oil. This residue was purified by flash chromatography (SiO2) with elution by hexane/CH2Cl2 (2:1), followed by hexane/CH2Cl2 (3:2) to give the title compound as a colorless oil (2.74 g, 79%).

Provenance & Evidence