ChemicalBook CAS DataBase List 5-Fluoro-2-methylaniline

5-Fluoro-2-methylaniline synthesis

6synthesis methods

Product Name:5-Fluoro-2-methylaniline
CAS Number:367-29-3
Molecular formula:C7H8FN
Molecular Weight:125.14

In a nitrogen-fed glovebox, Pd(P(o-tol)3)2 and CyPF-PtBu (1:1 ratio) were dissolved in dioxane and mixed for 5 min. A 20 mL scintation vial was charged with aryl halide (0.60 mmol, 1 equiv), ammonium sulfate (0.90 mmol, 1.5 equiv), and sodium tert-butoxide (2.7 mmol, 4.5 equiv). To this vial was added 6 mL of anhydrous dioxane and the appropriate amount of catalyst from the stock solution. The reaction vial was sealed with a Teflon-lined screw cap and removed from the glovebox. The reaction was stirred at the desired temperature for 12 h. The reaction mixture was diluted with EtOAc and filtered through a pad of Celite. The filtrate was concentrated in vacuo, and the crude product was purified by flash column chromatography. 5-Fluoro-2-methylaniline (Table 3, 2s) (CAS: 367-29-3) The reaction to form this product was conducted with 0.5 mol % Pd(P(o-tol)3)2 and 0.5 mol % CyPF-PtBu for 8 h. The crude product was isolated by flash column chromatography (5:1 Hexanes:EtOAc). 5-Fluoro-2-methylaniline was isolated as an oil in 76% yield. 1(600 MHz, CDCl3): δ 6.97 (t, J= 7.2 Hz, 1H), 6.40 (t, J= 9.9 Hz, 2H), 3.69 (s, 2H), 2.12 (s, 3H). 13C-NMR(151 MHz, CDCl3): δ 162.24 (d, JC-F= 240.9 Hz), 145.82 (d, JC-F= 10.6 Hz), 131.12 (d, JC-F= 9.6 Hz), 117.62 (d, JC-F = 2.6 Hz), 104.67 (d, JC-F= 21.0 Hz), 101.56 (d, JC-F= 24.6 Hz), 16.62 (s).
5-Fluoro-2-methylaniline synthesis

446-10-6 Synthesis

446-10-6
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$10.00/25 g

367-29-3
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$7.00/5g

Yield:367-29-3 70%

Reaction Conditions:

with hydrogenchloride;iron in ethanol;water at 0; for 12 h;Reflux;

Steps:

1.1 Step-i: Synthesis of 5-fluoro-2-methylaniline
4-Fluoro-1-methyl-2-nitrobenzene (2.50 g, 16 mmol) was dissolved in ethanol (50 mL).To this solution, iron powder (4.50 g, 81 mmol) and 0.25 ml of HC1 were added at 0 °C and the reaction mixture was refluxed for 12h. After completion of reaction, reaction mixture was cooled to room temperature, diluted with ethyl acetate, filtered through Celite and washed with ethyl acetate. Filtrate was basified with sodium bicarbonate solution; organic layer was washed with water followed by brine solution. Organic layer was dried over anhydrous Na2SO4 andconcentrated under reduced pressure to obtain crude compound. The residue was purified by column chromatography (n-hexane/ EtOAc 1:1) to give the title compound (1.4 g, 70 %) as a light brown solid.‘H NMR (400 MHz, DMSO-d6): ö 6.87 (t, J = 7.6 Hz, 1H), 6.38-6.34 (m, 1H), 6.22-6.18 (m, 1H), 5.11 (bs, 2H), 1.99 (s, 3H). MS (ES) mle: 126 (M+1).

References:

AURIGENE DISCOVERY TECHNOLOGIES LIMITED;GUMMADI, Venkateshwar Rao;SAMAJDAR, Susanta;GUPTA, Ajay WO2015/104662, 2015, A1 Location in patent:Page/Page column 37

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1422-53-3 Synthesis