Dichloromethane → 2,4,5-tribromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-Imidazole

To a solution of 2,4,5-tribromoimidazole (3.05 g, 10 mmol) in anhydrous DMF (50 mL) was added powdered K2CO3 (19 g, 137 mmol), and the resulting suspension was stirred vigorously and treated dropwise with SEMCl (2.3 g, 13.8 mmol). The suspension was then stirred vigorously overnight. The solid was filtered off and washed with fresh DMF (20 mL). The combined filtrates were then evaporated under reduced pressure. Methylene chloride (30 mL) was then added and the solution washed with 0.1 N Na2CO3 (3×50 mL), dried (Na2SO4), filtered and evaporated to give a residue, which was passed through a silica gel pad (CH2Cl2) and evaporated to give 3.6 g (83%) of the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 0.01 (s, 9H), 0.93 (t, 2H, J=8.0 Hz), 3.60 (t, 2H, J=8.0 Hz), 5.32 (s, 3H).

1. stirringThe suspension was then stirred vigorously overnight
2. filtrationThe solid was filtered off
3. washwashed with fresh DMF (20 mL)
4. customThe combined filtrates were then evaporated under reduced pressure
5. additionMethylene chloride (30 mL) was then added
6. washthe solution washed with 0.1 N Na2CO3 (3×50 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. customevaporated
10. customto give a residue, which
11. customevaporated

ORD record

ord-bc1318da3dad48eb8677beeb40b2f4ac

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07153848B2