Reference of 1835-65-0, A common heterocyclic compound, 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, molecular formula is C8F4N2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Synthesis of Exemplified Compounds (P-1-1), (P-2-1), and (P-3-1)Under nitrogen atmosphere, in 50 ml of 1-methyl-2-pyrrolidone, were dissolved 3.0 g (15 mmol) of tetrafluorophthalonitrile, 1.5 g (5.0 mmol) of synthesis intermediate (B), and 0.99 g (10 mmol) of copper chloride (I), and then stirred for 3 hours at 180¡ã C. After cooling the reaction mixture to room temperature, it was poured into 200 ml of a 5percent hydrochloric acid. Consequently, blue crystals were precipitated. These crystals were separated by a filtration under reduced pressure, followed by washing with water and then acetonitrile, and thereafter drying. Further, they were boiled with 50 ml of acetonitrile for 1 hour, and allowed to cool down to room temperature. The resultant precipitates were separated by a filtration under reduced pressure, and then dried. Thereby was obtained 2.2 g (Yield: 45percent) of a mixture (PP-1) (Melting point>200¡ã C.) containing the exemplified compounds (P-1-1), (P-2-1), and (P-3-1) of the present invention; and hexadecafluoro cupper phthalocyanine (F16CuPc).A mixing rate of phthalocyanine derivatives was measured by a liquid chromatography mass spectrometric analysis (LCMS). The result in terms of area ratio was as follows: (P-1-1):(P-2-1):(P-3-1):(F16CuPc)=54.0:26.4:4.1:15.5 (Since a molar absorption intensity of each of (P-1-1), (P-2-1), (P-3-1), and (F16CuPc) at a detecting wavelength of 254 nm is almost same, the ratio measured from the area results in equal to a molar ratio.).Measuring conditions: TSK gel ODS-80Ts (2 mm Phi.x.150 mm), elute: a mixed solution of A/B (volume ratio 3:7) from 0 minute to 15 minutes, and a mixed solution of A/B (volume ratio 15:85) from 15 minutes to 20 minutes) (elute A: water, elute B: a mixed solution of tetrahydrofuran/methanol (volume ratio 9:1)), flow rate: 0.2 ml/min, a detecting wavelength 254 nm, structural determination by atmospheric pressure chemical ionization (APCI)-mass spectrometry (MS) (It was confirmed using MS that a peak at the retention time=8.185 minutes was (F16CuPc), a peak at the retention time=11.676 minutes was (P-1-1), a peak at the retention time=13.905 minutes was (P-2-1), and a peak at the retention time=14.350 minutes was (P-3-1)). A peak was detected in the blank at the retention time of from 0 to 4 minutes, so that a measurement was started from 4 minutes.
The synthetic route of 1835-65-0 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; FUJIFILM Corporation; US7947826; (2011); B2;,
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