Toluene → 4-M-Bromophenyl-1-methylimidazole

Participants

Reaction Conditions

Reaction Steps

Using the method of Hazeldine et al., J. Chem. Soc., 125, 1431-41 (1924) a mixture of dimethylsulphate (145 μl, 1.53 mmol) and 4-m-bromophenyl imidazole (341 mg; 1.54 mmol) was stirred under N2 until the reaction mixture became extremely viscous. Toluene (150 μl) was added, and the mixture was heated at 100° C. for 1 hour. After cooling to ambient temperature, H2O (5 ml) was added, and the reaction mixture was brought to pH 9 with NaOH solution. It was then extracted with CH2Cl2 (2×10 ml). The organic layers were washed with brine, dried (MgSO4), and concentrated in vacuo to give 262 mg crude product mixed with starting material. Purification using preparative TLC on 2-1000μ Si Gel GF plates (eluting with 5% MeOH in CH2Cl2 and extracting with 10% MeOH in CH2Cl2) provided the product, 4-m-bromophenyl-1-methylimidazole (121 mg, 33% yield) as the least polar band.

Provenance & Evidence