Imidazole → (2-Bromo-5-(trifluoromethyl)benzyloxy)(tert-butyl)dimethylsilane

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To a solution of (2-bromo-5-(trifluoromethyl)phenyl)methanol (from Preparation 2, 10 g, 39 mmol) in DMF (20 mL) was added imidazole (5.87 g, 86.3 mmol) followed by t-butyldimethylsilyl chloride (7.11 g, 47.2 mmol) and the reaction was stirred at room temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography over 25+M Biotage silica column (eluted with 0-20% ethyl acetate in heptane) (5CV), 20% (1 CV) to afford a colorless oil (14 g, 97%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 0.15 (s, 6H) 0.98 (s, 9H) 4.75 (s, 2H) 7.36 (m, 1H) 7.60 (d, J=8.3 Hz, 1H) 7.84 (s, 1H)). GCMS: 311 (M-57, t-bu).

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