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 polyethyleneglycol 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 cyclohexane/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-aca7b4f44b014699b7dab0bcaa9a01df

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969552B2