N-bromobutanimide → HCID 89689977, compound

Participants

Reaction Steps

Sequentially add 1,8-diazabicyclo[5.4.0]undec-7-ene (51.6 mL, 345 mmol) and N-bromosuccinimide (34.6 g, 194 mmol) to a mechanically stirred suspension of 3-[3-[5-benzyloxy-2-ethyl-4-(4-fluorophenyl)phenoxy]propoxy]-2-propyl-benzamide (62.0 g, 114 mmol) in MeOH (620 mL) during which time the temperature raises from −4.1° C. to −3.2° C. over 1 min. Stir the reaction at −5° C. to −10° C. for 22 h. Add a solution of sodium bisulfate (25.1 g, 209 mmol, in 25 mL water) dropwise with stirring. Add water (620 mL) dropwise and stir 30 min at 10° C. Filter the suspension on a glass frit, wash the collected solid with water, and dry under vacuum to yield the title compound (65.8 g, quantitative) as an off-white powder. ES/MS m/z 572 (M+1).

Provenance & Evidence