Methyl 4-chlorobenzoate → HCID 58573710, compound

Temperature

-78 °C

Sodium bis(trimethylsilyl)amide (1 M in tetrahydrofuran, 117 mL) was slowly added to a −78° C. solution of 2-(3-chlorophenyl)acetic acid (10 g, 58.6 mmol) in tetrahydrofuran (58 mL) over 1 hour. After stirring at −78° C. for 40 minutes, a solution of methyl 4-chlorobenzoate (10 g, 58.6 mmol) in tetrahydrofuran (35 mL) was added over a period of 10 minutes. The reaction was stirred at −78° C. for 3 hours then allowed to warm to 25° C. After two hours at 25° C., the reaction was quenched with saturated aqueous ammonium chloride solution, and most of the tetrahydrofuran was removed under reduced pressure. The residue was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with saturated sodium chloride solution, dried over sodium sulfate, 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 hours
2. temperatureto warm to 25° C
3. waitAfter two hours at 25° C.
4. customthe reaction was quenched with saturated aqueous ammonium chloride solution
5. custommost of the tetrahydrofuran was removed under reduced pressure
6. extractionThe residue was extracted with ethyl acetate (2×100 mL)
7. washThe combined organic layers were washed with saturated sodium chloride solution
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationthe filtrate was concentrated
11. customThe product was recrystallized from ether/pentane

ORD record

ord-ca2352e930494ae3b3ab85ba219d53b0

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376386B2