Imidazole → 1-Bromo-4-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-methylethyl]benzene

tert-Butyldimethylsilyl chloride (2.10 g, 14 mmol) was added to a mixture of 2-(4-bromophenyl)-propan-2-ol (2.0 g, 9.3 mmol) and imidazole (0.95 g 14 mmol) in DMF (30 mL) and the resultant mixture was stirred at 80° C. for 24 h. The mixture was concentrated to one third of the original volume then diluted with water (50 mL) and extracted with diethyl ether (3×50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The resultant residue was purified by chromatography (silica, 50 g column, Si-SPE, 0-5% diethyl ether in pentane) to afford the title compound as a colourless oil (1.39 g, 46%). 1H NMR (MeOD, 400 MHz): 7.46-7.37 (m, 4H); 1.56 (s, 6H); 0.95-0.91 (m, 9H); 0.06 (s, 6H).

1. concentrationThe mixture was concentrated to one third of the original volume
2. additionthen diluted with water (50 mL)
3. extractionextracted with diethyl ether (3×50 mL)
4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. customevaporated in vacuo
7. customThe resultant residue was purified by chromatography (silica, 50 g column, Si-SPE, 0-5% diethyl ether in pentane)

ORD record

ord-2c7baa7ea61e4e0a8533c4198525119f

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501765B2