Hydrochloric Acid → HCID 178425332, compound

Temperature

40 °C

Under a nitrogen stream, a solution of magnesium (3.28 g, 4.01 equivalents), a small amount of iodine and 1,2-dibromoethane in THF (10 mL) was stirred at room temperature for 1.5 hrs. A solution of 5-bromo-m-xylene (25.2 g, 4.05 equivalents) in THF (100 mL) was added at 25° C., and the mixture was stirred at 40° C. for 40 min. A solution of diethyl phosphite (4.64 g, 33.6 mmol) in THF (5 mL) was added at −33° C., and the mixture was stirred at 0° C. for 30 min. Water (30 mL) was added at 3° C., and 6M-HCl (20 mL) and toluene (50 mL) were added. The mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned, and the organic layer was washed with 10% aqueous NaHCO3 solution (30 mL), and the organic layer was concentrated under reduced pressure. The residue was recrystallized from heptane and dried (reduced pressure, 50° C.) to give the title compound (6.80 g, white powder). yield 78.3%. melting point: 82.4° C.

1. stirringthe mixture was stirred at 0° C. for 30 min
2. stirringThe mixture was stirred at room temperature for 30 min
3. customThe reaction mixture was partitioned
4. washthe organic layer was washed with 10% aqueous NaHCO3 solution (30 mL)
5. concentrationthe organic layer was concentrated under reduced pressure
6. customThe residue was recrystallized from heptane
7. customdried (reduced pressure, 50° C.)

ORD record

ord-1a254e6152c14a09bfe99c8f4a6b834f

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07208633B2