Carbon Dioxide → 3-Cyclopropylbenzoic acid

1.6 M n-Butyllithium in hexanes (3.2 mL, 5.1 mmol) was added drop-wise to a solution of 1-bromo-3-cyclopropyl-benzene at −78° C. and stirred for 1 hour. This reaction mixture was then transferred via canula to a 250 mL round bottom flask equipped with a stirrer bar approximately ¼ full of solid carbon dioxide and stirred and for 1 hour. The reaction mixture was concentrated and then the residue was diluted with water. The aqueous layer was washed with dichloromethane (3×), acidified with 1 N HCl to pH˜2, and extracted with ethyl acetate. The organic phase was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford 3-cyclopropyl-benzoic (356 mg, 43%, white solid).

1. customThis reaction mixture was then transferred via canula to a 250 mL round bottom flask
2. stirringstirred and for 1 hour
3. concentrationThe reaction mixture was concentrated
4. additionthe residue was diluted with water
5. washThe aqueous layer was washed with dichloromethane (3×)
6. extractionextracted with ethyl acetate
7. washThe organic phase was washed with water and saturated brine
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customto afford 3-cyclopropyl-benzoic (356 mg, 43%, white solid)

ORD 기록

ord-2b2875ec77e54f688239d75101e02be0

출처 데이터셋

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07585881B2