8-Bromo-6-fluoro-2-methylquinazolin-4(3H)-one synthesis
- Product Name:8-Bromo-6-fluoro-2-methylquinazolin-4(3H)-one
- CAS Number:1352717-91-9
- Molecular formula:C9H6BrFN2O
- Molecular Weight:257.06
![8-Bromo-6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one](/CAS/20180703/GIF/1352717-90-8.gif)
1352717-90-8
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Yield:1352717-91-9 73.7%
Reaction Conditions:
with ammonia in water at 100; for 1.5 h;
Steps:
4.1.3. 8-Bromo-6-fluoro-2-methylquinazolin-4(3H)-one (13)
A suspension of 8-bromo-6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one (12, 466 mg, 1.81 mmol) in concd aqueous NH3 (28% v/v, 8 ml) was stirred at reflux (100 °C) for 1.5 h. The reaction mixture was concentrated. The resulting precipitate was collected by filtration, washed with water (20 ml) and dried to a constant weight to afford 8-bromo-6-fluoro-2-methylquinazolin-4(3H)-one (14, 342 mg, 73.7%) as a pale white solid, which was used without further purification: (tR=2.40 min, purity=100%), ESI+m/z, no ion detected; 1H NMR (DMSO-d6), δ (ppm) 2.39 (s, 3H), 7.80 (dd, J=3.0 Hz, JH-F=8.2 Hz, 1H), 8.13 (dd, J=2.7 Hz, JH-F=8.2 Hz, 1H), 12.54 (br s, 1H); 13C NMR (DMSO-d6) δ (ppm) 21.6, 110.7 (d, JC-F=23.0 Hz), 122.9 (d, JC-F=9.7 Hz), 123.0 (d, JC-F=8.8 Hz), 126.5 (d, JC-F=26.6 Hz), 143.9 (d, JC-F=2.7 Hz), 155.3 (d, JC-F=1.8 Hz), 159.0 (d, JC-F=247.7 Hz), 161.1 (d, JC-F=3.5 Hz); HRMS m/z (ESI+) calculated for C9H7N2BrF: 256.97203; found: 256.97205.
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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