[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:9][C:10]1[C:11]([CH3:20])=[C:12]2[C:16](=[CH:17][CH:18]=1)[CH:15]([OH:19])[O:14][CH2:13]2.N1C=CN=C1>C(Cl)Cl>[Br:9][C:10]1[C:11]([CH3:20])=[C:12]2[C:16](=[CH:17][CH:18]=1)[CH:15]([O:19][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[O:14][CH2:13]2A solution of TBS-Cl (3.63 g, 24.10 mmol) in methylene chloride (15 mL) was added to a solution of 5-bromo-4-methyl-1,3-dihydroisobenzofuran-1-ol (2.76 g, 12.1 mmol) and imidazole (1.72 g, 25.3 mmol) in methylene chloride (80 mL) at 0° C., the resulting solution was stirred at rt overnight. The mixture was partitioned between DCM and water, the water phase was extracted with methylene chloride and the combined organic phase was dried over sodium sulfate then concentrated, and the residue was purified on silica gel column using ethyl acetatehexane to give the title compound. LC/MS: (M−131)+: 210.91; 212.91.
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