Hydrochloric Acid → HCID 178427273, compound

Temperature

40 °C

In a stream of nitrogen, a solution of magnesium (58.41 g, 3.48 equivalents), a slight amount of iodine and 1,2-dibromoethane in tetrahydrofuran (400 mL) was stirred at room temperature for 1 hour. After addition of a solution of p-bromotoluene (411.11 g, 3.48 equivalents) in tetrahydrofuran (2000 mL) at 22° C., the mixture was stirred at 40° C. for 1 hour. Then, after addition of a solution of diethyl phosphite (94.76 g, 0.69 mol) in tetrahydrofuran (160 mL) at 20° C., the mixture was stirred at 24° C. for 30 minutes. 6M-HCl (320 mL) was added thereto at 4° C., followed by further addition of water (320 mL) and toluene (1000 mL), and the resulting mixture was stirred at a room temperature for 30 minutes. The reaction mixture was separated into layers, and the organic layer was successively washed with water (320 mL), an aqueous 5% NaHCO3 solution (320 mL) and an aqueous 5% NaCl solution (320 mL). The organic layer was filtered under reduced pressure, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from n-hexane and dried (under reduced pressure at 40° C.) to obtain the titled compound (87.12 g, white powder). The yield was 54.8%.

1. stirringthe mixture was stirred at 24° C. for 30 minutes
2. stirringthe resulting mixture was stirred at a room temperature for 30 minutes
3. customThe reaction mixture was separated into layers
4. washthe organic layer was successively washed with water (320 mL)
5. filtrationThe organic layer was filtered under reduced pressure
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe residue was recrystallized from n-hexane
8. customdried (under reduced pressure at 40° C.)

ORD record

ord-21dc43d072cf4996a6f053fb0caab5ad

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07541498B2