Hydrochloric Acid → HCID 178482907, compound

Temperature

5 °C

Under an argon atmosphere, a solution of magnesium (3.0 g, 1.0 equivalent) and a small amount of iodine in THF (30 mL) was stirred at room temperature for 1 hr. 4-Bromo-N,N-dimethylaniline (25 g, 0.125 moL) was added at 45° C., and the mixture was stirred at 5° C. for 1 hr. Then, diethyl phosphite (8.63 g, 0.50 equivalent) was added at 5° C., and the mixture was stirred at 5° C. for 1 hr. Water (30 mL) was added at 3° C., and then toluene (60 mL) and 6M-HCl (30 mL) were added. The mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned, and the aqueous layer was neutralized with NaOH and extracted with THF (30 mL). The combined 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 to give the title compound (9.53 g, slightly brown white crystals). yield 52.9%. melting point: 152.1° C.

1. stirringthe mixture was stirred at 5° C. for 1 hr
2. stirringThe mixture was stirred at room temperature for 30 min
3. customThe reaction mixture was partitioned
4. extractionextracted with THF (30 mL)
5. dry with materialThe combined 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

ORD record

ord-59b652f9d10e48439df437816ebcc0e5

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08053604B2