Carbon Dioxide → 2-Chloro-5-(trifluoromethyl)benzoic acid

The title compound was prepared according to the method described in Tetrahedron Lett., vol. 37, p. 2767 (1996). To a solution of 1-chloro-4-(trifluoromethyl)benzene (25.8 g, 143 mmol) and tetramethylethylene diamine (16.6 g, 143 mmol) in tetrahydrofuran (250 mL) cooled to −78° C., was added a solution of 1.6M butyllithium in hexane (89.4 mL, 143 mmol) was added dropwise under an argon atmosphere, and the mixture was stirred at the same temperature for 30 minutes. The solution was carefully poured onto crushed dry ice, and the resulting mixture was allowed to warm to room temperature. The solution was concentrated under reduced pressure, and the residue was poured into water. The solution was washed with diethylether, and subsequently made acidic by the addition of conc. hydrochloric acid, and organic matter was extracted with dichloromethane. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was crystallized from hexane to give the title compound (20.6 g, 64% yield). NMR (CDCl3) δ: 7.65. (1H, d, J=8.4 Hz), 7.75 (1H, dd, J=2.2 Hz. 8.4 Hz), 8.31 (1H, d, J=2.2 Hz), hidden (1H)

1. customThe title compound was prepared
2. additionwas added dropwise under an argon atmosphere
3. additionThe solution was carefully poured
4. concentrationThe solution was concentrated under reduced pressure
5. additionthe residue was poured into water
6. washThe solution was washed with diethylether
7. additionsubsequently made acidic by the addition of conc. hydrochloric acid, and organic matter
8. extractionwas extracted with dichloromethane
9. washThe extract was washed with saturated brine
10. dry with materialdried over anhydrous magnesium sulfate
11. customthe solvent was evaporated under reduced pressure
12. customThe residue thus obtained
13. customwas crystallized from hexane

ORD record

ord-de40962d36cc48d7a28b7ad66e0c3abb

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06949648B2