ChemicalBook CAS DataBase List Di-tert-butyl Chloromethyl Phosphate

Di-tert-butyl Chloromethyl Phosphate synthesis

13synthesis methods

Product Name:Di-tert-butyl Chloromethyl Phosphate
CAS Number:229625-50-7
Molecular formula:C9H20ClO4P
Molecular Weight:258.68

Di-tert-butyl (chloromethyl) phosphate, a key compound in the formation of many phosphon-oxymethyl pro-drugs, is prepared by reacting chloromethyl chlorosulfate (CMCS) with di-tert-butyl potassium phosphate (DTBPP) .

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68695-48-7 Synthesis

DI-TERT-BUTYLPHOSPHATE, TETRABUTYLAMMONIUM SALT

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Yield:229625-50-7 97%

Reaction Conditions:

at 20; for 4 h;Inert atmosphere;

Steps:

Di-tert-butyl (chloromethyl) phosphate.

Di-tert-butyl phosphate tetrabutylammonium salt (0.826 g, 1.83 mmol) was combined with chloroiodomethane (1.6 mL, 18.3 mmol) and was stirred at r.t. for 4 h during which time a precipitate formed. Tert-butyl methyl ether was then added and the mixture was vigorously stirred for 20 min resulting in the formation of a white precipitate. The precipitate was removed by filtration through a pad of Celite and the filtrate was concentrated. The resulting yellow oil was then taken up in tert-butyl methyl ether (16 mL) to precipitate additional salts. The mixture was filtered through a pad of Celite and the filtrate was concentrated and dried under vacuum to afford di-tert-butyl (chloromethyl) phosphate (0.457 g, 97% yield) as an oil: 1H NMR (500 MHz, CHLOROFORM-d) δ 5.62 (d, J=14.5 Hz, 2H), 1.50 (s, 18H).

References:

Hartz, Richard A.;Vrudhula, Vivekananda M.;Ahuja, Vijay T.;Grace, James E.;Lodge, Nicholas J.;Bronson, Joanne J.;Macor, John E. [Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,# 6,p. 1360 - 1363] Location in patent:supporting information

49715-04-0 Synthesis