5-bromoquinoline 1-oxide synthesis
- Product Name:5-bromoquinoline 1-oxide
- CAS Number:846038-45-7
- Molecular formula:C9H6BrNO
- Molecular Weight:224.05
4964-71-0
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Yield:846038-45-7 99%
Reaction Conditions:
with 3-chloro-benzenecarboperoxoic acid in dichloromethane at 20; for 3 h;
Steps:
9.A
To a solution of 5-bromoquinoline (2.5 g, 12.02 mmol) in DCM (50 mL) was added m-CPBA (3.50 g, 15.62 mmol) in three portions at room temperature. Upon completion of addition, the reaction mixture was stirred at room temperature for 3 h. After this time, IN NaOH (40 ml) was added to the reaction, and the resulting mixture was extracted with DCM (2 x 50 mL). The combined organic layers were washed with brine, dried over anhydrous MgS04, filtered, and concentrated to afford the title compound (2.7 g, 99% yield) as light yellow solid. LCMS, [M+H]+ = 223.9. XH NMR (400 MHz, CDC13) δ 8.75 (d, J= 8.8 Hz, 1H), 8.65 (d, J= 6.0 Hz, 1H), 8.18 (d, J= 8.8 Hz, 1H), 7.95 (d, J= 7.7 Hz, 1H), 7.68 - 7.56 (m, 1H), 7.44 (dd, J= 8.2, 6.0 Hz, 1H).
References:
WO2012/149236,2012,A1 Location in patent:Page/Page column 99
611-34-7
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