Dichloromethane → HCID 117660503, compound

Participants

Reaction Steps

To a mixture of a mixture (946 mg) of tert-butyl {[5-methoxy-1-(methoxymethyl)-1H-benzimidazol-2-yl]methyl}methylcarbamate and tert-butyl {[6-methoxy-1-(methoxymethyl)-1H-benzimidazol-2-yl]methyl}methylcarbamate and dichloromethane (10 mL) was added N-bromosuccinimide (527 mg) under ice-cooling, followed by stirring at room temperature overnight. The reaction mixture was diluted with EtOAc, and washed with a saturated aqueous NaHCO3 solution and brine in this order. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=85/15-60/40) to obtain a mixture (855 mg) of tert-butyl {[6-bromo-5-methoxy-1-(methoxymethyl)-1H-benzimidazol-2-yl]methyl}methylcarbamate and tert-butyl {[5-bromo-6-methoxy-1-(methoxymethyl)-1H-benzimidazol-2-yl]methyl}methylcarbamate.

Provenance & Evidence