Methyl 4-chlorobenzoate → HCID 58573710, compound

Temperature

-78 °C

To a solution of 2-(3-chlorophenyl)acetic acid (10 g, 58.6 mmol) in THF (58 ml) was added 117 mL of a 1M solution of sodium bis-(trimethylsilyl)amide in THF slowly over 1 h at −78° C. After being stirred at −78° C. for 40 min, a solution of methyl 4-chlorobenzoate (10 g, 58.6 mmol) in THF (35 ml) was added over a period of 10 min. The reaction was stirred at −78° C. for 3 h, then allowed to warm to 25° C., and stirred an additional 2 h until completion. The reaction was quenched with saturated aqueous NH4Cl solution and most of the THF was removed under reduced pressure. The residue was extracted with ethyl acetate (2×100 ml). The combined organic layers were washed with sat. NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated. The product was recrystallized from ether/pentane to provide the title compound as a white solid.

1. stirringThe reaction was stirred at −78° C. for 3 h
2. temperatureto warm to 25° C.
3. stirringstirred an additional 2 h until completion
4. customThe reaction was quenched with saturated aqueous NH4Cl solution and most of the THF
5. customwas removed under reduced pressure
6. extractionThe residue was extracted with ethyl acetate (2×100 ml)
7. washThe combined organic layers were washed with sat. NaCl solution
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationthe filtrate was concentrated
11. customThe product was recrystallized from ether/pentane

ORD record

ord-d19ebf322fad4e34822fd1883d70aea9

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569341B2