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ChemicalBook CAS DataBase List 3-Methylphenyl isothiocyanate
621-30-7

3-Methylphenyl isothiocyanate synthesis

11synthesis methods
-

Yield: 91%

Reaction Conditions:

with phenyllithium in tetrahydrofuran;diethyl ether at -40; for 0.000615 h;Flow reactor;

Steps:

5. Halogen-Li exchange reaction of m-, p-iodophenyl isothiocyanate with PhLiand reaction with various electrophiles using flow microreactors
General procedure: A microfluidic system consisting of two T-shaped micromixers (M1 and M2), two tube reactors (R1 and R2) andthree tube pre-temperature-retaining units (for P1, P2 and P3, 1 mm of inner diameter () and 100 cm of length(L)) were used. The microfluidic system was immersed in a temperature control bath. A solution of p-halophenylisothiocyanate or m-halophenyl isothiocyanate (0.1 M in THF) and a solution of phenyllithium reagents (0.44 Min diethyl ether) were individually introduced to M1 (: 250 μm) by syringe pumps. The resulting solution waspassed through R1 ( = 250 μm, L= 3.5 cm) and was mixed with a solution of electrophiles (0.3 M in THF) in M2(: 500 μm). The electrophiles were used as methyl triflate, trimethylsilyl triflate, methyl chloroformate, diethyloxalate, tributylstannyl chloride and NFSI. The resulting solution was passed through R2 (: 1 mm, L: 50 cm).After a steady state was reached, the product solution was collected for 30 s while being quenched with saturatedaqueous NH4Cl solution (2 mL).

References:

Lee, Hyune-Jea;Torii, Daiki;Jeon, Yongju;Yoshida, Jun-Ichi;Kim, Heejin [Synlett,2020,vol. 31,# 19,p. 1899 - 1902] Location in patent:supporting information

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