Imidazole → tert-Butyl(4-fluorobenzyloxy)dimethylsilane

To a solution of (4-fluoro-phenyl)-methanol (12.16 g, 96.4 mmol, 1.0 eq.) in anhydrous DMF (50 mL) at 0° C. under Ar was added imidazole (7.22 g, 106.1 mmol, 1.1 eq.) and tert-butyl-chloro-dimethyl-silane (15.99 g, 106.1 mmol, 1.1 eq.). After the addition was completed the cooling bath was removed and the reaction stirred for 18 h at rt. The reaction mixture was poured on ice, extracted with ethyl acetate (2×100 mL) and the combined organic phases washed with a sat. solution of sodium carbonate (2×100 mL) and sodium chloride (2×100 mL). The organic phase was dried over Na2SO4, concentrated by evaporation under reduced pressure yielding a brown oil that was purified by high vacuum destillation (bp 32-35° C. at 0.1 mbar) to give 23.0 g (99%) of the title compound. 1H NMR (400 MHz, CDCl3): δ0.00 (s, 6H), 0.84 (s, 9H), 4.60 (s, 2H), 6.89-6.94 (m, 2H), 7.16-7.20 (m, 2H). MS: 183.1 [M-tert-Bu]+.

1. additionAfter the addition
2. customwas removed
3. additionThe reaction mixture was poured on ice
4. extractionextracted with ethyl acetate (2×100 mL)
5. washthe combined organic phases washed with a sat. solution of sodium carbonate (2×100 mL) and sodium chloride (2×100 mL)
6. dry with materialThe organic phase was dried over Na2SO4
7. concentrationconcentrated by evaporation under reduced pressure
8. customyielding a brown oil that
9. customwas purified by high vacuum destillation (bp 32-35° C. at 0.1 mbar)

ORD record

ord-dfedc4d3b76041fb8577f05054fc1dab

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772253B2