Carbon Dioxide → 5-Benzoxy-2,3,4-trifluorobenzoic acid

Temperature

-78 °C

To a solution of diisopropylamine (10.14 g, 100.20 mmol) in THF (100 mL) was added n-BuLi (40.08 mL, 2.5 M in hexane, 100.20 mmol) at −78° C. under nitrogen atmosphere. The stirring was maintained at this temperature for 1 h. Then a solution of 1-benzyloxy-2,3,4-trifluorobenzene (19.89 g, 83.50 mmol) in THF (120 mL) was added. After stirring for 1 h at −78° C., the mixture was transferred to a bottle with dry ice. The mixture was stirred overnight at room temperature. The reaction was quenched with 10% aqueous HCl and pH was adjusted to 1-2. The mixture was extracted with ethyl acetate (100 mL×3). The combined organic extracts were washed with water (100 mL) and brine (100 mL) sequentially, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the desired product (white solid, 19.33 g, 82% yield). 1H NMR (400 MHz, CDCl3): δ 7.42 (m, 6H), 5.14 (s, 2H).

1. temperatureThe stirring was maintained at this temperature for 1 h
2. stirringThe mixture was stirred overnight at room temperature
3. customThe reaction was quenched with 10% aqueous HCl and pH
4. extractionThe mixture was extracted with ethyl acetate (100 mL×3)
5. washThe combined organic extracts were washed with water (100 mL) and brine (100 mL) sequentially
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-d07306e71e354492b2d32cb2fc3b4651

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290468B2