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

Temperature

-78 °C

To a solution of 1-bromo-2,3,4-trifluorobenzene (13.64 g, 64.6 mmol) in THF (120 mL) was added lithium diisopropylamide (2.0 M in THF, 33.9 mL, 67.8 mmol) at −78° C. under nitrogen atmosphere. 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 (300 mL) and extracted with ethyl acetate (200 mL×3). The combined organic extracts were washed with 5% sodium hydroxide (300 mL). The aqueous layer was acidized to pH 1 and extracted with ethyl acetate (200 mL×3). The combined organic extract was dried over Na2SO4, filtered and concentrated under reduced pressure to afford the desired product (white solid, 13.51 g, 82% yield). 1H NMR (400 MHz, CDCl3): δ 13.94 (s, 1H), 7.95 (m, 1H).

1. stirringThe mixture was stirred overnight at room temperature
2. customThe reaction was quenched with 10% aqueous HCl (300 mL)
3. extractionextracted with ethyl acetate (200 mL×3)
4. washThe combined organic extracts were washed with 5% sodium hydroxide (300 mL)
5. extractionextracted with ethyl acetate (200 mL×3)
6. extractionThe combined organic extract
7. dry with materialwas dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-4882f810fa4c41759a51c73a1d992d1f

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290468B2