Dibromodifluoromethane → Silane, [(4-bromo-4,4-difluoro-2-butynyl)oxy](1,1-dimethylethyl)dimethyl-

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Reaction Steps

To a solution of tert-butyl-dimethyl-prop-2-ynyloxy-silane (11.6 g, 6.78 mmol) in dry THF (190 mL) was added nBuLi (46.6 mL, 1.6 M solution in hexanes) dropwise (via an addition funnel) over 30 min at 0° C. under N2. The reaction mixture was stirred at rt for 1.5 h before being cooled to −78° C. Then, CF2Br2 (18.8 mL, 20.3 mmol) was added dropwise over 30 min. After stirring for 2.5 h at −78° C., the reaction mixture was quenched with a saturated solution of NH4Cl and was extracted with ether. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. Vacuum distillation (0.35-0.7 Torr) provided (4-bromo-4,4-difluoro-but-2-ynyloxy)-tert-butyl-dimethyl-silane (15.4 g, 76% yield) as a yellow liquid (55-70° C.): 1H NMR (400 MHz, CDCl3) δ0.15 (s, 6H), 0.93 (s, 9H), 4.46 (t, J=4.08 Hz, 2H); 19F NMR (376.19 MHz, CDCl3) δ −33.01 (t, J=4.1 Hz, 2F).

Provenance & Evidence