Hydrochloric Acid → HCID 178527031, compound

Temperature

3 °C

Under an argon atmosphere, a solution of magnesium (6.95 g, 1.0 equivalent) and a small amount of iodine in THF (70 mL) was stirred at room temperature for 1 hr. 1-Bromo-4-fluorobenzene (50 g, 0.286 moL) was added at 40° C., and the mixture was stirred at 3° C. for 1 hr. Then, diethyl phosphite (19.7 g, 0.50 equivalents) was added at 13 to 19° C., and the mixture was stirred at 5° C. for 1 hr. Water (45 mL) was added at 4° C., and toluene (150 mL) and 6M-HCl (45 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 water, 5% aqueous NaHCO3 solution (50 mL), and 5% aqueous NaCl solution (50 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered by gravity, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 30 g, n-hexane/ethyl acetate=1/0→3/1) to give the title compound (12.0 g, pale-red oil). yield 35.2%.

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. washthe organic layer was washed successively with water, 5% aqueous NaHCO3 solution (50 mL), and 5% aqueous NaCl solution (50 mL)
5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
6. filtrationfiltered by gravity
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe residue was purified by column chromatography (silica gel 30 g, n-hexane/ethyl acetate=1/0→3/1)

ORD record

ord-c99772246b79445d91c5ce9174d8e42e

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08053604B2