2,4-Dichloro-6-(3-fluorophenyl)-1,3,5-triazine synthesis

Yield:102528-19-8 56%

Reaction Conditions:

Stage #1: 3-fluorobromobenzenewith isopropylmagnesium chloride;lithium chloride in tetrahydrofuran at 20; for 3 h;Inert atmosphere;
Stage #2: 1,3,5-trichloro-2,4,6-triazine in tetrahydrofuran at 0 - 20; for 5 h;Inert atmosphere;

Steps:

6

Under an argon atmosphere, 3-bromofluorobenzene (560 μL, 5.0 mmol) was dissolved in THF (17 mL). To this solution, a THF solution (1.28 M, 4.1 mL, 5.3 mmol) of isopropyl magnesium chloride / lithium chloride complex was slowly added at room temperature, and the mixture was stirred for 3 hours. The reaction mixture was cooled to 0 ° C., cyanuric chloride (2.77 g, 15.0 mmol) was added, the temperature was raised to room temperature and stirred for 5 hours. Distilled water (3 mL) was added to the reaction mixture, and the mixture was stirred at 50 ° C. for 1 hour, then allowed to cool to room temperature, and chloroform was added. The resulting insoluble matter was separated by filtration and washed with chloroform and water. The organic layer was separated and the aqueous layer was extracted twice with chloroform. The organic layers were combined, washed with water and dried over sodium sulfate. After removing the solid by filtration, the low-boiling fraction was removed under reduced pressure, and the obtained residue was dried under vacuum to obtain a crude product. The obtained crude product was purified by silica gel chromatography (eluent: hexane / chloroform) to obtain the target 4,6-dichloro-2- (3-fluorophenyl) -1,3,5-triazine (56% , 685 mg, 2.8 mmol).

References:

JP2017/160144,2017,A Location in patent:Paragraph 0074-0075