Bromine → HCID 66742191, compound

Participants

Reaction Steps

In round bottom flask with reflux condenser was placed 2.54 g acetic acid 2-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-(1-methyl-6-oxo-5-trimethylsilanyl-1,6-dihydro-pyridazin-3-yl)-benzyl ester, 5.51 g potassium bromide, 4.55 g potassium acetate, followed by ca 18.4908 g bromine. The mixture warmed on addition of the bromine. The mixture was stirred for 2 minutes at room temperature, then set in a bath at 55° C. and stirred. A stopper was placed lightly in the top of the reflux condenser to contain the bromine vapors. After 70 minutes, the mixture was cooled to room temperature, excess bromine removed under a stream of nitrogen. The mixture was taken up in 500 mL of dichloromethane, washed 1×150 mL brine, containing 12 g sodium bisulfite with some resultant exotherm, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by chromatography on silica gel (Silicycle 120 g, 3.5×21.5 cm, 207 vol), applied in dichloromethane, eluting with dichloromethane-ethyl acetate (80:20), followed by chromatography on silica gel (Silicycle 120 g, 3.5×21.5 cm, 207 vol), applied in dichloromethane, eluting with dichloromethane-ethyl acetate (80:20) to afford the desired product (1.91 g) as an off white solid.

Provenance & Evidence