These common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, 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. Application In Synthesis of 2-(4-Chlorophenoxy)aniline
A solution of 2-(4-chloro-phenoxy)-phenylamine (298 mg, 1.4 mmol), N-(2-acetyl- phenyl)-acetamide, (200 mg, 1.13 mmol) and chlorotriisopropoxytitanium IV (0.53 ml, 2.26 mmol) in toluene (15 ml) was stirred at r.t. for 4 days. NaHCO3 was added and the mixture was extracted repeatedly with EtOAc, dried (MgSO4) and evaporated to dryness. The residue was re-dissolved in THF (20 ml) and cooled to 0 C, to this was added succinic acid (270 mg, 2.26 mmol) and borane (IM in THF, 2.3 ml, 2.26 mmol). The reaction was slowly warmed to r.t. and stirred for 8 h. NaHCO3 was added and the volatile solvents removed in vacuo, the mixture was then extracted with EtOAc and dried (MgSO4). The crude material was purified by flash chromatography (0-100 % DCM in hexane) to yield the product, 79 mg, 19 % yield. LCMS: tr= 1.42 min (95 % MeOH in water), m/z M-H 365.33, HPLC: U= 4.49 min (90 % ACN in water), 97 %,1H NMR (CDCl3, 270 MHz,): delta 1.17 (3H, X, J = 12 Hz, CH3CH2), 1.56 (3H, d, J = 6.7 Hz, CH3CH), 3.10 (2H, q, J= 14.1 Hz, CH2), 4.22 (IH, d, J= 6.0 Hz, NH), 4.53 (IH, q, J = 13.3 Hz, CH), 4.59 (IH, br.s, NH), 6.66-6.93 (7H, m, ArH), 7.01 (IH, td, J= 7.9, 1.5 Hz, ArH), 7.16-7.31 (4H, m, ArH).13C NMR (CDCl3, 68 MHz): 14.9, 19.9 (CH3), 38.1 (CH2), 50.9 (CH), 111.1, 113.6, 117.0, 118.0, 118.6, 119.5, 125.5, 126.5 (ArCH), 128.6, 127.8 (ArC), 128.3, 129.7 (ArCH), 13.7, 143.3, 146.7, 156.4 (ArC).HRMS: Calcd for C22H23ClN2O (M+Na)+ 389.1386, found (M+Na)+ 389.1391.
The synthetic route of 2-(4-Chlorophenoxy)aniline has been constantly updated, and we look forward to future research findings.
Reference:
Patent; STERIX LIMITED; WO2009/66072; (2009); A2;,
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