Hydrochloric Acid → 3-Iodo-2-ethylbenzoic acid

Temperature

-50 °C

A n-butyllithium-1.58M n-hexane solution (36.2 ml, 57.2 mmol) was added dropwise to a solution of diisopropylamine (8.02 ml, 57.2 mmol) in tetrahydrofuran (114 ml) under ice-cooling, and the mixture was further stirred for 30 minutes. After the reaction mixture was cooled to −50° C., a solution of 3-iodo-2-methylbenzoic acid (5.00 g, 19.1 mmol) in tetrahydrofuran (38 ml) was added thereto. After the mixture was stirred for 1 hour, iodomethane (9.51 ml, 153 mmol) was added thereto and the temperature of the mixture was raised from −50° C. to −20° C. over 1 hour. The reaction mixture was poured into 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was successively washed with 1N hydrochloric acid, water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 3-iodo-2-ethylbenzoic acid (5.48 g, yield: 100%).

1. temperaturecooling
2. stirringAfter the mixture was stirred for 1 hour
3. temperaturethe temperature of the mixture was raised from −50° C. to −20° C. over 1 hour
4. extractionextracted with ethyl acetate
5. washThe organic layer was successively washed with 1N hydrochloric acid, water
6. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
7. customThe solvent was removed under reduced pressure

ORD record

ord-f8f0438a8cea4534a5db4b69db0a7cca

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923573B2