22236-08-4, name is 3-(Difluoromethoxy)aniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 22236-08-4
To a solution of 3- (difluoromethoxy) aniline (318 mg, 2.0 iranol) and pyridine (633 mg, 8.0 iranol) in N-methylpyrrolidone (2 mL) was added phenyl chloroformate (251 muL, 2.0 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. 2-chloro-4- [ (5-methyl-5H-pyrrolo [3, 2-d]pyrimidin-4- yl) oxy] aniline (275 mg, 1.0 mmol) was added to the reaction mixture, and the mixture was stirred at 800C for 8 hr. The reaction mixture was diluted with water, basified with IN aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane/ethyl acetate=80/20->0/100) , and then silica gel column chromatography (hexane/ethyl acetate=80/20-»0/100) and recrystallized from diisopropyl ether to give the title compound (229 mg, 50%) as a white solid. 1H-NMR (DMSO-de, 300 MHz) delta 4.11 (3H, s) , 6.61 (IH, d, J = 3.0 Hz), 6.81 (IH, dd, J = 8.0, 2.1 Hz), 7.19 – 7.23 (IH, m) , 7.22 (IH, t, J = 74.1 Hz), 7.31 (IH, dd, J = 9.0, 2.7 Hz), 7.35 (IH, t, J = 8.0 Hz), 7.49 (IH, t, J = 2.1 Hz), 7.56 (IH, d, J = 2.7 Hz), 7.80 (IH, d, J = 3.0 Hz), 8.17 (IH, d, J = 9.0 Hz), 8.30 (IH, s), 8.43 (IH, br s) , 9.60 (IH, br s) .
The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/4749; (2007); A1;,
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