Water → (2-Bromoethoxy)-tert-butyldimethylsilane

To a stirred solution of bromoethanol (9.912 g, 79.32 mmol) in dry DCM (25 ml) was added in one portion tert-butyldimethylsilyl chloride (13.212 g, 85.03 mmol) and the reaction mixture stirred at room temperature. A solution of triethylamine (8.865 g, 12.3 ml, 87.61 mmol) in dry DCM (40 ml) was then added dropwise over 1 h and 20 min. The reaction mixture was stirred at room temperature for 3 d, then water (30 ml) was added. The organic phase was separated and the aqueous phase was extracted with DCM (2×20 ml). The combined organic extracts were washed with brine (30 ml), dried (Na2SO4), and the solvent removed under reduced pressure to give a pale yellow oil. Distillation under reduced pressure gave the title compound (10.54 g, 55%) as a colourless oil.

1. stirringThe reaction mixture was stirred at room temperature for 3 d
2. customThe organic phase was separated
3. extractionthe aqueous phase was extracted with DCM (2×20 ml)
4. washThe combined organic extracts were washed with brine (30 ml)
5. dry with materialdried (Na2SO4)
6. customthe solvent removed under reduced pressure
7. customto give a pale yellow oil
8. distillationDistillation under reduced pressure

ORD record

ord-e74c3a8f85c2458d90b74ff5893aee3b

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895313B2