6-Fluoroindole synthesis
- Product Name:6-Fluoroindole
- CAS Number:399-51-9
- Molecular formula:C8H6FN
- Molecular Weight:135.14
![Hydrazinecarboxamide, 2-[2-(4-fluoro-2-nitrophenyl)ethylidene]-, (2E)-](/CAS/20210305/GIF/1065183-63-2.gif)
1065183-63-2
399-51-9
The general procedure for the synthesis of 6-fluoroindole from the compound (CAS: 1065183-63-2) is as follows: Intermediate 110: Synthesis of 6-fluoro-1H-indole. In a 1 L high-pressure reactor, (4-fluoro-2-nitrophenyl)acetaldehyde semicarbazone (27.0 g, 0.110 mol) was suspended in THF (750 mL) with stirring. To this suspension was added a slurry of Rh/C (5 wt%) in toluene and Fe(OAc)2 (2.9 g, 0.017 mol), where the amount of Rh was 3.5 g, 0.002 mol. The reactor was charged with H2 to 50 atm and the reaction was stirred for 2 days at room temperature. After completion of the reaction, the mixture was filtered through a diatomaceous earth pad and washed with MeOH (150 mL). The filtrate was concentrated to give a black oil, which was partitioned between DCM (500 mL) and water (300 mL). The organic layer was separated and the aqueous phase was extracted with DCM (2 x 200 mL). The organic phases were combined, washed with brine (200 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was dissolved in DCM (100 mL) and decolorized by a fast silica gel column. After filtration, the filtrate was concentrated under reduced pressure to give 12.9 g (87% yield) of 6-fluoroindole. 1H NMR (300 MHz, DMSO-d6) δ: 11.11 (1H, s), 7.49 (1H, dd, J = 8.6, 5.5 Hz), 7.30 (1H, t, J = 2.4 Hz), 7.13 (1H, dd, J = 10.3, 2.4 Hz), 6.81 (1H, ddd, J = 11.0, 7.6, 2.4 Hz), 6.40-6.38 (1H, m).
1065183-63-2
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399-51-9
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Yield:399-51-9 87%
Reaction Conditions:
with hydrogen;iron(II) acetate;5% rhodium-on-charcoal in tetrahydrofuran;toluene at 20; under 38002.6 Torr; for 48 h;Inert atmosphere;
Steps:
110
Intermediate 110: 6-Fluoro-1H-indole. To a stirred suspension of (1￡)-(4-fluoro-2-nitrophenyl)ethanal semicarbazone (27.0 g, 0.1 10 mol) in THF (750 ml.) in a 1 L bomb was added Rh/C (5 %; 3.5 g, 0.002 mol Rh) slurried in toluene and Fe(OAc)2 (2.9 g, 0.017 mol). The bomb was charged with H2 to 50 atm and stirred at room temperature for 2 days. The reaction mixture was filtered through celite, washing with MeOH (150 ml_). The filtrate was concentrated to give a black oil that was partitioned between DCM (500 ml.) and water (300 ml_). The layers were separated and the aqueous fraction was extracted with DCM (2 x 200 ml_). The combined organic extracts were washed with brine (200 ml_), dried (Na2SO4), and concentrated under reduced pressure. The residue was dissolved in DCM (100 ml.) and treated with flash silica to decolourise the solution. The mixture was filtered concentrated under reduced pressure, giving 12.9 g (87 %) of the title compound. 1H NMR: (300 MHz; DMSO-d6) δ 11.1 1 (1 H, s), 7.49 (1 H, dd, J=8.6 & 5.5), 7.30 (1 H, t, J=2.4), 7.13 (1 H, dd, J=10.3 & 2.4), 6.81 (1 H, ddd, J=1 1.0, 7.6 & 2.4) and 6.40-6.38 (1 H, m).
References:
WO2008/118724,2008,A1 Location in patent:Page/Page column 126
2343-23-9
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120192-70-3
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3093-97-8
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399-51-9
350 suppliers
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