Bromobenzene → Ethyl 3,4-dihydro-4-phenyl-2H-1,4-benzoxazine-2-carboxylate

Temperature

100 °C

Tris(dibenzylideneacetone)dipalladium (0) (4.3 mg, 0.0046 mmol), xantphos (8.2 mg, 0.014 mmol), and bromobenzene (40 □L, 0.381 mmol) were added to a solution of (±)-ethyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate (65 mg, 0.31 mmol) in dioxane (2.5 mL). The solids were allowed to dissolve, and cesium carbonate (143 mg, 0.44 mmol) was added, and the suspension was stirred at 100° C. for 24 h. The mixture was cooled to ambient temperature, diluted with water (20 mL), and the product was extracted with 67% EtOAc/hexane (3×25 mL). The organic layers were combined, dried over sodium sulfate, and concentrated. Purification of the crude concentrate by flash column chromatography using 15% EtOAc/hexane afforded the title compound. MS m/z: 284 (M+1).

1. dissolutionto dissolve
2. temperatureThe mixture was cooled to ambient temperature
3. extractionthe product was extracted with 67% EtOAc/hexane (3×25 mL)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated
6. customPurification of the crude
7. concentrationconcentrate by flash column chromatography

ORD record

ord-378c8d6cc1b242259dac99d498f4cb3c

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07872009B2