Tetrahydrofuran → Cyclopropyl(2-fluorophenyl)methanone

To a stirred mixture of 10 parts of magnesium and 72 parts of tetrahydrofuran there were added portionwise 50 parts of bromocyclopropane, keeping the temperature below 10° C. At reflux temperature, there was added a solution of 50 parts of 2-fluorobenzenecarbonitrile in 72 parts of tetrahydrofuran. Stirring at reflux temperature was continued until completion of the reaction. The reaction mixture was cooled on ice (0°-5° C.) and decomposed with a mixture of ice, water and acetic acid. The product was extracted with trichloromethane (3×) and the combined extracts were washed with water (2×), dried, filtered and evaporated. The residue was distilled (1.33 Pa; 78°-105° C.) (2×), yielding 19.8 parts (29.4%) of cyclopropyl (2-fluorophenyl)methanone; bp. 100°-103° C. (at 1.3 Pa) (interm. 17).

1. customthe temperature below 10° C
2. temperatureAt reflux temperature, there
3. temperatureat reflux temperature
4. customwas continued until completion of the reaction
5. temperatureThe reaction mixture was cooled on ice (0°-5° C.)
6. extractionThe product was extracted with trichloromethane (3×)
7. washthe combined extracts were washed with water (2×)
8. customdried
9. filtrationfiltered
10. customevaporated
11. distillationThe residue was distilled (1.33 Pa; 78°-105° C.) (2×)

ORD record

ord-dd59f4d1793c4dc8b2ea867236e0dbb1

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05556886