These common heterocyclic compound, 33348-34-4, name is 4-Amino-3-iodobenzonitrile, 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. Product Details of 33348-34-4
tert-Butyl 4-amino-3-iodobenzylcarbamate In an oven-dried three-necked round bottom flask provided with a reflux condenser was 4-Amino-3-benzonitrile (1.0 g, 4.1 mmol) dissolved in anhydrous THF (10 ml) under N2. BH3.THF was added dropwise. Once the addition was complete the reaction mixture was refluxed for 2 h. The mixture was allowed to cool and HCl (2.0 N aq.) (6.0 ml) was added dropwise. Then the mixture was refluxed for 1.0 h. The solvents were removed under vacuum and residue was suspended in CH2Cl2 (30 ml). DMAP (100.1 mg, 0.8 mmol), Et3N (1.3 ml, 9.4 mmol) and Boc2O (2.7 g, 12.3 mmol) were added and the mixture stirred at r.t. for 1.5 h. H2O was added and the product extracted with EtOAc.The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography (CH2Cl2/MeOH 99:1) affording 1.0 g (71%) of the title compound.1H NMR (CDCl3) delta 7.55 (d, 1H), 7.07 (dd, 1H), 6.70 (d, 1H), 4.76 (bs, 1H), 4.15 (d, 2H), 4.08 (bs, 2H), 1.46 (s, 9H).
The synthetic route of 4-Amino-3-iodobenzonitrile has been constantly updated, and we look forward to future research findings.
Reference:
Patent; RESPIRATORIUS AB; US2012/40942; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com