Phenethyl bromide → 1-Phenethyl-1H-imidazole-4-carbaldehyde

Imidazole-4-carboxaldehyde (6.73 g, 70 mmol) was added portionwise to a suspension of sodium hydride (1.68 g, 60% dispersion in mineral oil, 70 mmol) in tetrahydrofuran (280 ml), and the mixture was then stirred at room temperature for 30 minutes. (2-Bromoethyl)benzene (9.56 ml, 70 mmol) was added, and the mixture was stirred at room temperature for 72 hours. The mixture was evaporated under reduced pressure and the residue was partitioned between water (300 ml) and dichloromethane (500 ml), and the layers were separated. The organic phase was dried (MgSO4) and evaporated under reduced pressure. The crude product was pre-adsorbed onto silica gel, and purified by column chromatography on silica gel using an elution gradient of ethyl acetate:pentane (50:50 to 100:0) to afford the title compound, 1.44 g. 1H-NMR (CDCl3, 400 MHz) δ: 3.16 (t, 2H), 4.23 (t, 2H), 7.02 (d, 2H), 7.28 (m, 3H), 7.36 (s, 1H), 7.50 (s, 1H), 9.83 (s, 1H). LRMS: m/z (ES+) 223 [MNa+].

1. stirringthe mixture was stirred at room temperature for 72 hours
2. customThe mixture was evaporated under reduced pressure
3. customthe residue was partitioned between water (300 ml) and dichloromethane (500 ml)
4. customthe layers were separated
5. dry with materialThe organic phase was dried (MgSO4)
6. customevaporated under reduced pressure
7. custompurified by column chromatography on silica gel using an elution gradient of ethyl acetate:pentane (50:50 to 100:0)

ORD record

ord-31441750fe72498fa9d8520b043eb1a1

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06713496B2