[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.N1C=CN=C1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][Si:20]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22])=[C:4]([CH3:10])[CH:3]=1Dissolve 4-bromo-2,6-dimethylphenol (30.16 g, 150 mmol) and imidazole (26.6 g, 390 mmol) in CH2Cl2. Added t-butyldimethylchlorosilane (36.17 g, 240 mmol) and stirred mechanically for 3 h. The solids were vacuum filtered and the filtrate concentrated. Suspended the resulting residue in water and extracted with ethyl acetate (2×150 mL). The combined organic portions were washed with water (150 mL) and brine (150 mL) and then dried (Na2SO4), filtered and concentrated in vacuo to give a light brown oil. Purify on a Waters Prep 2000 LC (hexanes) to give 40.96 g of the title compound as a clear liquid. 1H NMR(CDCl3): δ6.91 (s, 2H), 2.00 (s, 6H), 0.86 (s, 9H), 0.01 (s, 6H).
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