Hydrochloric Acid → HCID 178527025, compound

Temperature

40 °C

Under an argon atmosphere, a solution of magnesium (2.94 g, 1.0 equivalent), a small amount of iodine and a small amount of 1,2-dibromoethane in THF (30 mL) was stirred at room temperature for 1 hr. A solution of 2-bromonaphthalene (25 g, 0.121 mol) in THF (20 mL) was added at 35°. The mixture was stirred at 40° C. for 30 min. and then stirred at 5° C. for 30 min. Then, a solution of diethyl phosphite (9.77 g, 0.5 equivalent) in THF (10 mL) was added at 5° C., and the mixture was stirred at 5° C. for 3 hrs. Water (20 mL) was added at 3° C. and then toluene (60 mL) and 6M—HCl (20 mL) were added. The mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned, and the organic layer was washed successively with water (10 mL), 5% aqueous NaHCO3 solution (10 mL) and 5% aqueous NaCl solution (10 mL). Then the organic layer was dried over anhydrous magnesium sulfate, filtered by gravity, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from diisopropyl ether-heptane to give the title compound (9.62 g, white crystals). yield 53.0%. melting point: 98.3° C.

1. stirringstirred at 5° C. for 30 min
2. stirringthe mixture was stirred at 5° C. for 3 hrs
3. stirringThe mixture was stirred at room temperature for 30 min
4. customThe reaction mixture was partitioned
5. washthe organic layer was washed successively with water (10 mL), 5% aqueous NaHCO3 solution (10 mL) and 5% aqueous NaCl solution (10 mL)
6. dry with materialThen the organic layer was dried over anhydrous magnesium sulfate
7. filtrationfiltered by gravity
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe residue was recrystallized from diisopropyl ether-heptane

ORD record

ord-edc1f3fdac3b41d1a1c57dd5ae240870

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678942B2