Hydrochloric Acid → HCID 178425332, compound

Temperature

5 °C

Under an argon atmosphere, a solution of magnesium (25 g, 0.95 equivalent) and a small amount of iodine in THF (250 mL) was stirred at room temperature for 1 hr. 5-Bromo-m-xylene (200 g, 1.08 moL) was added at 48° C., and the mixture was stirred at 5° C. for 1 hr. Diethyl phosphite (78.3 g, 0.52 equivalent) was added at 5° C., and the mixture was stirred at 5° C. for 2 hrs. Water (200 mL) was added at 3° C., and toluene (200 mL) and 6M-HCl (160 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 (100 mL), 5% aqueous NaHCO3 solution (100 mL) and 5% aqueous NaCl solution (100 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered by gravity. The filtrate was concentrated under reduced pressure and the residue was recrystallized from diisopropyl ether-heptane to give the title compound (43.3 g, white crystals). yield 33.3%.

1. stirringthe mixture was stirred at 5° C. for 2 hrs
2. stirringThe mixture was stirred at room temperature for 30 min
3. customThe reaction mixture was partitioned
4. washthe organic layer was washed successively with water (100 mL), 5% aqueous NaHCO3 solution (100 mL) and 5% aqueous NaCl solution (100 mL)
5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
6. filtrationfiltered by gravity
7. concentrationThe filtrate was concentrated under reduced pressure
8. customthe residue was recrystallized from diisopropyl ether-heptane

ORD record

ord-25896a45a0854fefb9003df21721d8cf

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07208633B2