5-bromo-7-fluoroquinoline synthesis
- Product Name:5-bromo-7-fluoroquinoline
- CAS Number:1239462-97-5
- Molecular formula:C9H5BrFN
- Molecular Weight:226.05
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Yield:-
Reaction Conditions:
with ferrous(II) sulfate heptahydrate;sulfuric acid in nitrobenzene at 80;
Steps:
1.94.3
To 3-bromo-5-fluoroaniline hydrochloride (2.9 g, 12.89 mmol) was added glycerol (1.9 mL, 25.99 mmol), nitrobenzene (1.3 mL), sulfuric acid (3.5 mL) and iron (II) sulfate heptahydrate (0.23 g, 0.82 mmol). The reaction mixture was placed in an oil bath set at 80 0C and stirred overnight followed by basification with 12Ν NaOH and extraction with dichloromethane. The organic phase was collected, dried (sodium sulfate), filtered and concentrated under reduced pressure. Purification by flash chromatography (silica, 50:50 ethyl acetate/hexane) gave 5-bromo-7-fluoroquinoline and 7-bromo-5-fluoroquinoline (1.03 g, 30%) Retention time (min) = 1.877 and 1.967, method [4], MS(ESI) 227.9 (M+H).
References:
ELAN PHARMACEUTICALS, INC.;SHAM, Hing, L.;KONRADI, Andrei, W.;HOM, Roy, K.;PROBST, Gary, D.;BOWERS, Simeon;TRUONG, Anh;NEITZ, R., Jeffrey;SEALY, Jennifer;TOTH, Gergely WO2010/91310, 2010, A1 Location in patent:Page/Page column 164
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