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-ef6b8afa825a467996e6eaf7f26a9c17

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08383641B2