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 75 tetrahydrofuran (30 mL) was stirred at room temperature for 1 hr. After addition of 4-bromo-N,N-dimethylaniline (25 g, 0.125 moL) at 45° C., the mixture was stirred at 5° C. for 1 hr. After addition of diethyl phosphite (8.63 g, 0.50 equivalent) at 5° C., the mixture was stirred at 5° C. for 1 hr. Water (30 mL) was added to the mixture at 3° C., and toluene (60 mL) and 6M hydrochloric acid (30 mL) were added thereto, and the mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned, and the aqueous layer was neutralized with sodium hydroxide and extracted with tetrahydrofuran (30 mL). Then, the combined organic layer was dried over anhydrous magnesium sulfate and filtered naturally, 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 tetrahydrofuran (30 mL)
5. dry with materialThen, the combined organic layer was dried over anhydrous magnesium sulfate
6. filtrationfiltered naturally
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe residue was recrystallized from diisopropyl ether

ORD record

ord-a51c230bc18d46a58c671240b80b4724

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08981147B2