Dimethylformamide → HCID 67278503, compound

Participants

Reaction Conditions

Reaction Steps

149 g (0.875 mol) of 4 and 97.2 g (0.875 mol) of triphenylphosphine (TPP) dissolved in 300 mL of dimethylformamide (DMF) maintained under argon at 22° C., to which was added dropwise 159.8 g (0.875 mol) of bromine. The mixture was stirred for 24 hrs. 2.5 L of ethyl acetate was then added to the reaction mixture and, after stirring an additional one hour, the organic layer was washed with 4×800 mL of water, 1 L saturated NaHCO3, and 700 mL brine. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in 1.5 L of hexane, stirred at 10° C. 2 hrs, and filtered. High vacuum distillation gave the product 5 in 74% yield (151 g). HPLC retention time 9.1 min, Bp 72-74° C. at 0.25 mm Hg. The reaction is shown as follows:

Provenance & Evidence