Reference of 60702-69-4, A common heterocyclic compound, 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, molecular formula is C7H3ClFN, 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.
To a freshly-prepared solution of LDA (33.7 mmol) in anhydrous THF (30 mL) at -78Cwas added a solution of commercially available 2-chloro-4-fluorobenzonitrile (5.00 g,32.1 mmol) in THF (10 mL), dropwise at such a rate that the internal temperature remained < -70 C. The mixture was stirred for 2 h and a solution of iodine (8.97 g, 35.4 mmol) in THE (20 mL) was added dropwise (temp < -70 C). The mixture was stirred 30 min, removed from the cooling bath and quenched by addition of 10% Na2S2O3. Themixture was poured into water and extracted with EtOAc (x3). Combined organics were washed (water, brine), dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in a small amount of CH2Cl2 and filtered through a pad of silica (25% EtOAc/hexanes eluent). Fractions containing the major product were concentrated in vacuo and the residue was recrystallized from heptane affording 3.24 g tan solid. Themother liquor was concentrated and the residue was purified by flash chromatography (EtOAc / hexanes, gradient elution) affording 2.85 g of a pale yellow solid. Solids were combined to give 2-chloro-4-fluoro-3-iodobenzonitrile (6.09 g, 67 % yield): 1H NMR (400MHz, CDCl3) delta 7.70 (dd, J = 8.6, 5.5 Hz, 1 H), 7.08 (dd, J = 8.6, 6.8 Hz, 1 H); MS (GCMS EI) m/z 281 ([M]+, 100%).
The synthetic route of 60702-69-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; TURNBULL, Philip, Stewart; CADILLA, Rodolfo; WO2014/13309; (2014); A1;,
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