Trimethylaluminum → HCID 178508525, compound

Temperature

0 °C

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.

1. temperaturewarmed to 100° C
2. waitAfter 5 h
3. temperaturethe solution was cooled to 0° C.
4. customquenched with aqueous NaOH (2N, 90.0 ml)
5. extractionThe suspension was extracted with EtOAc (4×90 ml)
6. customthe combined extracts were dried
7. filtrationover then filtered through Celite®
8. concentrationThe solution was concentrated
9. customthe residue triturated with EtOAc

ORD record

ord-d58ce02a7ece4810a01b1625e65cd247

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09303043B2