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

温度

-78 °C

To a solution of 1-benzyloxy-2,3,4-trifluorobenzene (19.89 g, 83.6 mmol) in anhydrous THF (120 mL) was added lithium diisopropylamide (2.0 M in THF, 42.6 mL, 85.2 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 (20.0 g, 454.5 mmol). The mixture was stirred overnight at ambient temperature. The reaction was quenched with 10% aqueous HCl (300 mL). The mixture was 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 with concentrated HCl (aq.) and extracted with ethyl acetate (200 mL×3). The combined organic layer was 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 14.01 (s, 1H), 7.42 (6H, m), 5.16 (2H, s).

1. stirringThe mixture was stirred overnight at ambient temperature
2. customThe reaction was quenched with 10% aqueous HCl (300 mL)
3. extractionThe mixture was extracted 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. dry with materialThe combined organic layer was dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORDレコード

ord-b0415606abca4aa39c2cf277bb4d52e7

出典データセット

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09290468B2