Application of 153898-63-6,Some common heterocyclic compound, 153898-63-6, name is 2-Iodo-5-methoxyaniline, molecular formula is C7H8INO, 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.
NaBH(OAc)3 (5.10 g, 24.1 mmol) was added to a solution of p-anisaldehyde (0.41 mL, 6.63 mmol), 2-iodo-5-methoxyaniline5 (1.5 g, 6.02 mmol) and AcOH (0.11 mL, 0.11 mmol) in 1,2-DCE (30 mL). The mixture was stirred 24 h, then saturated aq. KHCO3 (15 mL) was slowly added while stirring vigorously. The aqueous layer was extracted with EtOAc, the combined organic layer was washed with brine, dried over MgSO4, and volatile compounds were removed under vacuum. The residue was subjected to flash chromatography (20% EtOAc in hexanes) to give the title compound (1.80 g, 81%). 1H NMR (400 MHz, CDCl3) delta 7.50 (d, J = 8.6 Hz, 1H), 7.26 (d, J= 8.6 Hz, 2H), 6.87 (d, J= 8.6 Hz, 2H), 6.14 (d, J = 2.8 Hz, 1H), 6.07 (dd, J = 8.6 Hz, 2.8 Hz, 1H), 4.49 (s, 1H), 4.27 (s, 1H), 4.26 (s, 1H), 3.78 (s, 3H), 3.69 (s, 3H); 13C NMR (100 MHz, CDCl3) delta 161.2, 158.8, 147.9, 138.9, 130.3, 128.5, 114.0, 104.0, 97.9, 74.5, 55.2, 47.8
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodo-5-methoxyaniline, its application will become more common.
Reference:
Article; Zhang, Hanmo; Hay, E. Ben; Geib, Stephen J.; Curran, Dennis P.; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1649 – 1655;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com