Imidazole → 4-Bromobenzyloxy-tert-butyldimethylsilane

tert-Butyldimethylsilyl chloride (2.42 g, 16 mmol) was added to a mixture of (4-bromophenyl)methanol (2.0 g, 107 mmol) and imidazole (1.09 g, 16 mmol) in DMF (30 mL) and the resultant mixture was stirred at ambient temperature for 72 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 (3.21 g, 100%). 1H NMR (CDCl3, 400 MHz): 7.45-7.42 (m, 2H); 7.21-7.17 (m, 2H); 4.68 (s, 2H); 0.93 (s, 9H); 0.09 (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-7110ab8e98634d348bee0746fcf318e3

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501765B2