Hydrochloric Acid → HCID 178425926, compound

Temperature

40 °C

Under a nitrogen stream, a solution of magnesium (3.60 g, 3.50 equivalents) and a small amount of iodine and 1,2-dibromoethane in THF (25 mL) solution was stirred at room temperature for 30 min. A solution of m-bromotoluene (25.36 g, 3.51 equivalents) in THF (130 mL) was added at 24° C., and the mixture was stirred at 40° C. for 30 min. Then, a solution of diethyl phosphite (5.84 g, 42.3 mmol) in THF (10 mL) was added at 25° C., and the mixture was stirred at 24° C. for 1.5 hrs. 6M-HCl (20 mL) was added at 4° C., and then water (20 mL) and toluene (60 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 10% aqueous NaHCO3 solution (20 mL), water (20 mL) and 10% aqueous NaCl solution (20 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered by gravity, and further passed through a membrane filter (0.2 μm) under reduced pressure. The filtrate was concentrated under reduced pressure to give the title compound (9.09 g, colorless oil). yield 93.3%

1. stirringthe mixture was stirred at 24° C. for 1.5 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 10% aqueous NaHCO3 solution (20 mL), water (20 mL) and 10% aqueous NaCl solution (20 mL)
5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
6. filtrationfiltered by gravity
7. filtrationfilter (0.2 μm) under reduced pressure
8. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-b77d01617b0e409fa88c1d5d7d05c013

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08053604B2