2-Bromoethanol → 1-(2-Bromo-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

Participants

Reaction Steps

To the stirred solution of 1-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (100 mg, 0.34 mmol), 2-Bromo-ethanol (0.03 mL, 0.41 mmol) and triphenylphosphine (107 mg, 0.41 mmol) in THF (2.0 mL) is added DIAD (0.082 mL, 0.41 mmol) in a dropwise manner. The mixture is stirred at room temperature for 20 hr and then another 0.03 mL of 2-Bromo-ethanol, 107 mg of triphenylphosphine and 0.08 mL of DIAD are added. The reaction is continued for another 24 hr and then the solvent is removed under vacuum and the residue is purified by flash column chromatography to give 75 mg (55%) of 1-(2-Bromo-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one.

Provenance & Evidence