反应详情

Magnesium metal (98.2 g) was stirred with 100 ml of anhydrous ether under nitrogen for 1 hr. 4-Fluorobromobenzene (700 g) was dissolved in 1750 ml of anhydrous ether. A 20 ml aliquot of the solution was added to the magnesium metal to initiate reaction. Once reflux had begun, the 4-fluorobromobenzene solution was added at such a rate as to maintain a gentle reflux. After the addition was complete, the mixture was heated under reflux for 1 hr. Ethyl cylopropylcarboxylate (180.6 g) was dissolved in 500 ml of anhydrous ether. After the Grignard solution had been cooled to ambient temperature, the solution was added dropwise such that a gentle reflux was maintained. After complete addition of the ester, the mixture was heated under reflux for 45 mins and cooled to ambient temperature. The reaction mixture was quenched with 500 ml of saturated aqueous ammonium chloride and 2 l of ice water. The ether layer was separated and the aqueous layer was extracted twice with ether. The ether extracts were combined and washed with water and saturated brine. The ethereal mixture was dried over sodium sulfate, filtered and the solvent removed under vacuum to provide a quantitative yield or cyclopropyl-bis-(4-fluorophenyl)methanol.

1. customreaction
2. temperatureOnce reflux
3. temperatureto maintain a gentle reflux
4. additionAfter the addition
5. temperaturethe mixture was heated
6. temperatureunder reflux for 1 hr
7. additionthe solution was added dropwise such that
8. temperaturea gentle reflux
9. temperaturewas maintained
10. temperaturethe mixture was heated
11. temperatureunder reflux for 45 mins
12. temperaturecooled to ambient temperature
13. customThe reaction mixture was quenched with 500 ml of saturated aqueous ammonium chloride and 2 l of ice water
14. customThe ether layer was separated
15. extractionthe aqueous layer was extracted twice with ether
16. washwashed with water and saturated brine
17. dry with materialThe ethereal mixture was dried over sodium sulfate
18. filtrationfiltered
19. customthe solvent removed under vacuum