Carbon Dioxide → 2,6-Dichloro-4-methylbenzoic acid

Temperature

-78 °C

To a stirred solution of 1,3-dichloro-5-methylbenzene (2.0 g, 12.4 mmol) in THF (20 mL) was added n-BuLi (2.0 M in hexane, 9.3 mL, 18.6 mmol) at −78° C. dropwise over a period of 10 min and mixture was stirred at −78° C. for 30 min. A dry-ice was added to the reaction mixture slowly and the mixture was stirred at the same temperature for 20 min. Thereafter, the reaction mixture was slowly warmed to room temperature, quenched with 6 M HCl (10 mL) and extracted with EtOAc (2×30 mL). The combined organic layers were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to get compound A111-1 (1.1 g, 44%) as a white solid.

1. stirringthe mixture was stirred at the same temperature for 20 min
2. temperatureThereafter, the reaction mixture was slowly warmed to room temperature
3. customquenched with 6 M HCl (10 mL)
4. extractionextracted with EtOAc (2×30 mL)
5. washThe combined organic layers were washed with water (50 mL), brine (50 mL)
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated under reduced pressure
8. customto get compound A111-1 (1.1 g, 44%) as a white solid

ORD record

ord-3f07e0d7b89d4426bc76e42a197b7638

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365522B2