These common heterocyclic compound, 263351-43-5, name is tert-Butyl 3-iodobenzylcarbamate, 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 tert-Butyl 3-iodobenzylcarbamate
tert-Butyl 3-iodobenzylcarbamate (0.67 mmol) was dissolved in 1 mL of dry DMF and the resultant solution was evacuated to 40 mm pressure and then released to N2 (g) three times. Triethylamine (1:8 ratio with DMF, 100 muL), Pd(PPh3)2Cl2 (0.030 mmol), and CuI (0.067 mmol) were added. The resultant mixture evacuated to 40 mm pressure for Ca. 30 seconds and then released to N2 (g). Finally, the alkyne 4 (0.67 mmol) in DMF (0.07 M) was added dropwise via an addition funnel over 40 minutes. The reaction mixture was stirred at room temperature for 18 hr and then diluted with ethyl acetate, poured into 0.1 M HCl and extracted with EtOAc (3¡Á100 mL). The combined organic layers were washed with water and brine and dried over MgSO4. The extract was concentrated and the product purified by Biotage chromatography (40M, product loaded onto SiO2) with 2% MeOH/CH2Cl2 to afford the desired title compound: 1H NMR (400 MHz, DMSO-d6) delta 8.24 (m, 1H), 7.50 (dd, J=4, 16 Hz, 1 H), 7.41 (m, 1H), 7.26 (m, 3H), 7.18 (m, 2H), 7.05 (m, 1H), 4.71 (m, 1H), 4.08 (m, 3H), 3.70 (dd, J=4, 12 Hz, 1H), 3.62 (m, 4H), 3.40 (m, 2H), 2.92 (m, 4H), 2.47 (m, 4H), 1.83 (s, 3H), 1.79 (m, 2H), 1.38 (s, 9H).
The synthetic route of tert-Butyl 3-iodobenzylcarbamate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Harris, Christina Renee; US2004/204463; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com