Allyl bromide → 4-methyl-1-(prop-2-en-1-yl)-1h-imidazole

4-Methylimidazole (2.0 g, 24.36 mmol), allyl bromide (2.2 mL, 24.36 mmol), N,N-diisopropylethylamine (5.0 mL, 29.24 mmol) in DMF (50 mL) were stirred at 80° C. overnight. Then the reaction mixture was cooled, quenched with saturated NaHCO3 (30 mL), and extracted with CH2Cl2 (4×40 mL). The combined organic layers were dried (MgSO4), filtered, concentrated, and dried in vacuo to afford a brown oil. Purification by flash column chromatography on silica using 2% CH3OH/CH2Cl2 afforded the product as a yellow oil (1.13 g, 40%). 1H NMR (CDCl3) (as a mixture of regio-isomers) δ 2.17 and 2.22 (s, total 3H), 4.44-4.48 (m, total 2H), 5.19-5.24 (m, total 2H), 5.89-6.00 (m, total 1H), 6.61 and 6.79 (s, total 1H), 7.35 and 7.39 (s, total 1H).

1. temperatureThen the reaction mixture was cooled
2. customquenched with saturated NaHCO3 (30 mL)
3. extractionextracted with CH2Cl2 (4×40 mL)
4. dry with materialThe combined organic layers were dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customdried in vacuo
8. customto afford a brown oil
9. customPurification by flash column chromatography on silica using 2% CH3OH/CH2Cl2

ORD record

ord-9eb6d160729e4d809ff3302c46d039f9

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354932B2