tert-Butyldimethylsilyl chloride → 1071455-00-9

Temperature

0 °C

A mixture of 3-bromophenyl acetic acid (1 g, 4.6 mmol), t-butyldimethylsilylchloride (1.6 g, 10.7 mmol) and THF (15 ml) were stirred at 0° C. under nitrogen. Lithium diisopropyl amide (5 ml-2M solution in heptane) was added to the mixture drop wise and the reaction was allowed to proceed first at 0° C., then at room temperature over night. The solvent was removed in vacuo and the crude material was redissolved in acetonitrile (20 ml). Selectfluor (2.1 g, 6.0 mmol) in acetonitrile (40 ml) was added drop wise and the reaction was allowed to stir at room temperature overnight. Solvent was removed under vacuum, redissolved in ethyl acetate and extracted with 1N HCl. The organic layer was dried with Na2SO4, decanted, and concentrated to dryness. Silica chromatography of the crude using a gradient of ethyl acetate and hexane afforded (3-bromo-phenyl)-fluoro-acetic acid (436 mg, 40% yield). 1H NMR (500 MHz, DMSO-d6) δ 6.0-6.1 (d, 1H), 7.44 (m, 2H), 7.62 (m, 2H).

1. customto proceed first at 0° C.
2. waitat room temperature over night
3. customThe solvent was removed in vacuo
4. dissolutionthe crude material was redissolved in acetonitrile (20 ml)
5. stirringto stir at room temperature overnight
6. customSolvent was removed under vacuum
7. dissolutionredissolved in ethyl acetate
8. extractionextracted with 1N HCl
9. dry with materialThe organic layer was dried with Na2SO4
10. customdecanted
11. concentrationconcentrated to dryness

ORD record

ord-d827060db7a64b6a8a0fc86d3fdc9a3e

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242280B2