Extracurricular laboratory: Synthetic route of 3-Iodophenyl acetate

The synthetic route of 42861-71-2 has been constantly updated, and we look forward to future research findings.

Reference of 42861-71-2, A common heterocyclic compound, 42861-71-2, name is 3-Iodophenyl acetate, molecular formula is C8H7IO2, 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.

Step A Heck Coupling Trans-Ethyl-7-{[3-(3-Hydroxy-phenyl)-allyl]-methanesulfonyl-amino}-heptanoate To a solution of 7-(allyl-methanesulfonyl-amino)-heptanoic acid ethyl ester (250 mg, 0.86 mmol), 1-acetyloxy-3-iodo-benzene (225 mg, 0.86 mmol), and triethylamine (139 mL, 1 mmol) in DMF (3 mL) was added palladium acetate (25 mg). The reaction was heated to 80 C. under nitrogen for 24 h. The mixture was cooled to room temperature and aqueous sodium thiosulfate and CH2Cl2 were added. The aqueous solution was extracted with CH2Cl2 (2*) and the combined organic layers were washed with water (1*) and brine (1*). The organic solution was dried with MgSO4, filtered, and concentrated in vacuo. The product was purified by radial chromatography (hexanes to 25% EtOAc/hexanes) to afford the title compound of Step A (95 mg). 1H NMR (CDCl3 400 MHz) delta 6.88-7.34 (m, 4H), 6.53-6.60 (m, 1H), 6.13-6.20 (m, 1H), 4.10 (q, 2H), 3.95 (d, 2H), 3.17-3.21 (m, 2H), 2.85 (s, 3H), 2.24-2.31 (m, 2H), 2.31 (s, 3H), 1.56-1.62 (m, 4H), 1.27-1.33 (m, 4H), 1.23 (t, 3H).

The synthetic route of 42861-71-2 has been constantly updated, and we look forward to future research findings.