3-Fluoro-4-methylaniline synthesis

4synthesis methods

Product Name:3-Fluoro-4-methylaniline
CAS Number:452-77-7
Molecular formula:C7H8FN
Molecular Weight:125.14

1427-07-2

452-77-7

General procedure for the synthesis of 3-fluoro-4-methylaniline from 2-fluoro-4-nitrotoluene: Freshly distilled toluene (0.6 mL), aromatic nitro compounds (0.60 mmol), indium triiodide (InI3, 14.9 mg, 0.030 mmol) and 1,1,3,3-tetramethyldi siloxane (TMDS, 318 μL, 1.80 mmol). After sealing the vial with a polytetrafluoroethylene (PTFE) septum, the mixture was stirred at 60 °C (bath temperature) and the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, 5 mL of aqueous sodium bicarbonate (NaHCO3) was added to the mixture, which was then extracted with ethyl acetate (EtOAc, 3 × 6 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: n-hexane-ethyl acetate, from 9:1 to 4:1) to obtain the target product 3-fluoro-4-methylaniline.

1427-07-2
367 suppliers
$6.00/5g

452-77-7
285 suppliers
$8.00/5g

Yield:452-77-7 74%

Reaction Conditions:

with indium (III) iodide;1,1,3,3-Tetramethyldisiloxane in toluene at 60; for 6 h;Inert atmosphere;Sealed tube;chemoselective reaction;

Steps:

Reductive Conversion of Nitrobenzenes into Anilines; General Procedure
General procedure: To a screw top vial (5 mL) under N2 containing freshly distilled toluene (0.6 mL) were successively added an aromatic nitro compound (0.60 mmol), InI3 (14.9 mg, 0.030 mmol), and TMDS (318 μL, 1.80 mmol). After the vial was sealed with a cap that contained a PTFE septum, the mixture was stirred at 60 °C (bath temperature), and monitored via TLC analysis. Sat. aq NaHCO3 solution (5 mL) was added to the resultant mixture, which was then extracted with EtOAc (3 × 6 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (n-hexane-EtOAc, 9:1 to 4:1) to afford the corresponding aniline derivative.

References:

Sakai, Norio;Asama, Shun;Konakahara, Takeo;Ogiwara, Yohei [Synthesis,2015,vol. 47,# 20,art. no. SS-2015-F0275-OP,p. 3179 - 3185]

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