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

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).

1. temperaturebefore being cooled to −78° C
2. stirringAfter stirring for 2.5 h at −78° C.
3. customthe reaction mixture was quenched with a saturated solution of NH4Cl
4. extractionwas extracted with ether
5. washThe combined organic extracts were washed with brine
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. distillationVacuum distillation (0.35-0.7 Torr)

ORD record

ord-27e89d829fbb42d4af0a5d47a051dcd5

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07884124B2