1,3-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-benzene synthesis

Yield:120951-86-2 99%

Reaction Conditions:

with 1H-imidazole in dichloromethane at 20; for 16 h;

Steps:

81 Preparation 81I ,3-Bis((tert-butyldimethylsi IyI)oxy)benzene

To resorcinol (2.00 g, 18.2 mmol) and imidazole (3.71 g, 54.5 mmol) dissolved in DCM (40 mL) was added tert-butyldimethylchlorosilane (8.21 g, 54.5 mmol). A precipitate formed andfurther DCM (40 mL) was added, before stirring for 16 hours at room temperature under nitrogen. The reaction was filtered and the filtrate was concentrated in vacuo. The residue was purified using silica gel column chromatography (Biotage SP1, 120 g silica column, eluting with 0-10% EtOAc in heptane) to afford the title compound as a colourless oil (6.18 g, >99%). LCMS Method C: Rt = 5.39 mins, ES MS mlz 339.3 [M+H]1H NMR (400 MHz, CDCI3): O ppm 6.95 (1H, t), 6.35 (2H, dd), 6.25 (1H, t), 1.85 (18H, 5), 0.10 (12H, 5).

References:

WO2017/60729,2017,A1 Location in patent:Page/Page column 87