Potassium Fluoride → ((S)-2-Fluoro-1-methyl-ethyl)-benzene

Temperature

62.5 °C

9.62 g of toluene-4-sulfonic acid (S)-2-phenyl-propyl ester (33.13 mmol) were dissolved in 80 ml of polyethylenglycol 400. 9.62 g of potassium fluoride (165.6 mmol) were added and the reaction mixture was stirred at 50° C. for 3 days and another 2 days at 55-70° C. The reaction was treated with 150 ml of saturated aqueous sodium chloride solution, extracted three times with diethyl ether, and the combined organic layers were dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified via silica gel chromatography using cyclohexyane/ethyl acetate 15% as eluent. 2.85 g of the desired product were isolated, containing ˜25% of the elimination side product.

1. extractionextracted three times with diethyl ether
2. dry with materialthe combined organic layers were dried over magnesium sulfate
3. filtrationfiltered
4. customthe solvent was evaporated under reduced pressure
5. customThe crude product was purified via silica gel chromatography

ORD record

ord-7f9f9bbfbd8f4c358d51841e9af10522

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08470810B2