1-Chloromethylnaphthalene → 2-(2-Naphthalen-1-yl-ethyl)-benzonitrile

Temperature

-78 °C

5.6 mL (9.0 mmol) of n-butyllithium, 1.6 M in hexanes, was added to a solution of 1.26 mL (911 mg, 9.00 mmol) of diisopropylamine in 50 mL of THF (tetrahydrofuran) was cooled to −78° C. under nitrogen and via syringe. The mixture was stirred at −78° C. for 1 hour and a solution of 353 mg (3.00 mmol) of α-tolunitrile in 10 mL of THF was added. The solution was stirred at −78° C. for one additional hour and a solution of 1.57 mL (9.00 mmol) of HMPA and 583 mg (3.30 mmol) of 1-chloromethylnaphthalene in 10 mL of THF was added dropwise. After stirring for one additional hour at −78° C., the reaction was quenched with water and extracted with Et2O (diethyl ether) (2×30 mL). The organic layer was washed with aqueous 1 N HCl (30 mL), water (3×30 mL), brine (30 mL) and dried (Na2SO4). The solvent was evaporated to give 735 mg of crude product which is used directly next steps.

1. stirringThe solution was stirred at −78° C. for one additional hour
2. stirringAfter stirring for one additional hour at −78° C.
3. customthe reaction was quenched with water
4. extractionextracted with Et2O (diethyl ether) (2×30 mL)
5. washThe organic layer was washed with aqueous 1 N HCl (30 mL), water (3×30 mL), brine (30 mL)
6. dry with materialdried (Na2SO4)
7. customThe solvent was evaporated

ORD record

ord-d8e1cf8b25a0478eb8f4a3106f1542ca

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07375125B2