Trimethylaluminum → HCID 178508525, compound

Participants

Reaction Conditions

Reaction Steps

To a flask was charged 37 (9.00 g, 32.4 mmol) and toluene (90.0 ml). The suspension was cooled to 0° C. and was added trimethylaluminum (1.8 equiv., 58.4 mmol, 2M in toluene) drop-wise over 30 minutes. The suspension was then stirred at room temperature for 1 h and then warmed to 100° C. After 5 h, the solution was cooled to 0° C. and quenched with aqueous NaOH (2N, 90.0 ml). The suspension was extracted with EtOAc (4×90 ml) and the combined extracts were dried over then filtered through Celite®. The solution was concentrated and the residue triturated with EtOAc to afford 8-bromo-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-imine 33 (6.26 g, 26.0 mmol, 80% yield) as white crystalline solid.

Provenance & Evidence