8-Bromo-6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one synthesis
- Product Name:8-Bromo-6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one
- CAS Number:1352717-90-8
- Molecular formula:C9H5BrFNO2
- Molecular Weight:258.04
259269-84-6
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Yield:1352717-90-8 94%
Reaction Conditions:
at 140; for 2 h;
Steps:
4.1.2. 6-Fluoro-8-bromo-2-methyl-4H-3,1-benzoxazin-4-one (12)
2-Amino-3-bromo-5-fluorobenzoic acid (472 mg, 2.02 mmol) in Ac2O (4 ml) was stirred at reflux (140 °C) for 2 h. The reaction mixture was allowed to cool to room temperature. The reaction mixture was concentrated to dryness and diluted with ethyl acetate (10 ml). The reaction mixture was concentrated to dryness to give the desired 8-bromo-6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one (12, 490 mg, 94%) as a pale brown solid, which was used without further purification: LCMS (tR=3.42 min, purity=100%), ESI+m/z, no ion detected; 1H NMR (DMSO-d6), δ (ppm): 2.44 (s, 3H), 7.89 (dd, 1H, J=2.7 Hz, JH-F=7.8 Hz), 8.25 (dd, 1H, J=2.7 Hz, JH-F=8.2 Hz); 13C NMR (DMSO-d6), δ (ppm) 21.1, 112.9 (d, JC-F=23.9 Hz), 119.1 (d, JC-F=9.7 Hz), 121.6 (d, JC-F=9.7 Hz), 127.7 (d, JC-F=26.5 Hz), 141.0 (d, JC-F=2.7 Hz), 159.4 (d, JC-F=1.8 Hz), 159.6 (d, JC-F=250.3 Hz), 168.6.
References:
Barlaam, Bernard;Harris, Craig S.;Lecoq, Jonathan;Nguyen, Ha Thi Hoang [Tetrahedron,2012,vol. 68,# 2,p. 534 - 543] Location in patent:experimental part
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