Boron tribromide → HCID 66645648, compound

Participants

Reaction Conditions

Reaction Steps

Under N2, a 50 mL round-bottomed flask was charged with a 1M solution of BBr3 (3.11 mL, 3.11 mmol), then cooled in an ice/brine bath. To the cooled solution, was added drop-wise, 6-methoxy-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one 394B (0.2 g, 1.035 mmol) in anhydrous DCM (4 mL). The reaction was stirred under N2 and then allowed to slowly warm to 23° C. After 2 hr, ice cold water (25 mL) was slowly added to the reaction mixture. The product was collected by vacuum filtration, washed with water, and dried in vacuo to give a light tan solid (0.116 g, 62.5% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.37 (d, J=6.57 Hz, 3H) 4.44-4.57 (m, 1H) 6.24-6.32 (m, 1H) 6.36 (d, J=2.78 Hz, 1H) 6.74 (d, J=8.59 Hz, 1H) 9.15 (s, 1H) 10.50 (s, 1 H). ESI-MS: m/z 180.1 (M+H)+.

Provenance & Evidence