Electric Literature of 22236-08-4, A common heterocyclic compound, 22236-08-4, name is 3-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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.
General procedure: A solution of cyanic bromide [Caution, highly toxic] (2 equiv) in diethyl ether (10 mL) was added dropwise to a solution of the appropriately substituted aniline (1 equiv) in diethyl ether (10 mL) at 0 C. After complete addition the mixture was warmed to ambient temperature and stirred 1-20 h, which was followed by TLC. Solids were filtrated and washed with ether. The filtrate was washed with 1 M HCl (25 mL) followed by brine (25 mL). The organic layer was collected, dried over anhydrous MgSO4, filtrated and evaporated to dryness under reduced pressure. 5.1.32 N-(3-(Difluoromethoxy)phenyl)cyanamide (24h) The reaction of 3-(difluoromethoxy)aniline (23h) (1.60 g, 10.0 mmol) according to procedure A yielded, after purification over silica with ethyl acetate/petroleum ether (60-80) (25/75, v/v), the title compound as a light brown oil which solidified upon standing (683 mg, 3.71 mmol, 37%); Rf 0.24 (ethyl acetate/petroleum ether (60-80), 25/75, v/v). 1H NMR (CDCl3) delta 7.31-7.22 (m, 2H, HAryl), 6.87-6.76 (m, 2H, HAryl), 6.77 (s, 1H, NH), 6.48 (t, JHF = 73.5 Hz, 1H, CHF2). 13C NMR (CDCl3) delta 152.30 (Ar-O), 138.96 (Ar-N), 131.18 (Ar), 117.84 (t, CHF2, JCF = 260.72 Hz), 114.37 (Ar), 112.48 (Ar), 111.13 (NCN), 107.24 (Ar).
The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Klein, Pieter J.; Christiaans, Johannes A.M.; Metaxas, Athanasios; Schuit, Robert C.; Lammertsma, Adriaan A.; Van Berckel, Bart N.M.; Windhorst, Albert D.; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 1189 – 1206;,
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