Bromotrimethylsilane → P-(12,12,13,13,14,14,15,15,15-Nonafluoropentadecyl)-phosphonic acid

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Reaction Steps

To a solution of 15.23 g of 1-(diethylphosphono)-11-(nonafluorobutyl)undecane in 40 mL of dichloromethane was added 11.50 g of bromotrimethylsilane. After 24 hr at room temperature, the solution was concentrated to a pale yellowish liquid, and the intermediate silylphosphonate ester was dissolved in 200 mL of methanol. The resultant solution was stirred at room temperature for 30 min and concentrated to a white solid. Dissolution in methanol and concentration were repeated two times, and two recrystallizations of the crude product from heptane gave 10.85 g of 1-phosphono-11-(nonafluorobutyl)undecane (CF3(CF2)3(CH2)11PO3H2) as colorless plates, m.p. 93-96° C.

Provenance & Evidence