67963-68-2

Colourless Oil

Step 1a: 4-Bromophenol (10.0 g, 57.8 mmol) and tert-butyldimethylchlorosilane (TBSCl, 11.3 g, 75.14 mmol) were sequentially added to dry DMC (100 mL). Triethylamine (Et3N, 16.7 g, 115.6 mmol) was slowly added dropwise at room temperature, and the reaction mixture was continued to be stirred for 2 h after the dropwise addition. After completion of the reaction, the solvent was removed by distillation under reduced pressure. Petroleum ether (200 mL) was added to the residue, transferred to a partition funnel, and the organic layer was washed sequentially with water and saturated saline. The organic layer was dried with anhydrous sodium sulfate (Na2SO4), filtered and purified by a short silica gel column, and finally the solvent was evaporated under reduced pressure to give the target product (4-bromophenoxy)tert-butyldimethylsilane (compound 0101, 16.6 g, 100% yield) as a colorless oil.1H NMR (CDCl3) δ: 0.18 (s, 6H), 0.98 (s, 9H), and 2.71 (t, J = 6 Hz, 2H), 6.70-6.73 (m, 2H), 7.30-7.33 (m, 2H).

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[2] Bioorganic and medicinal chemistry, 2003, vol. 11, # 16, p. 3457 - 3474
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[4] Patent: US2009/76006, 2009, A1. Location in patent: Page/Page column 29; 34-35
[5] Patent: EP747704, 2003, B1. Location in patent: Page 11