Benzene, 2-chloro-4-ethyl-1-methoxy- synthesis

Yield:1369850-65-6 58 %Chromat.

Reaction Conditions:

with iodobenzene;toluene-4-sulfonic acid;3-chloro-benzenecarboperoxoic acid;lithium chloride in tetrahydrofuran at 20; for 24 h;regioselective reaction;

Steps:

A typical procedure for the catalytic chlorination of electron-rich aromatic compounds:

General procedure: To THF (4mL), anisole (0.3mmol, 32mg), TsOH·H₂O (0.3mmol, 57.1mg), mCPBA (75%, 0.3mmol, 69mg), PhI (0.12mmol, 25mg) and LiCl (0.36mmol, 16mg) were added. The mixture was stirred at r.t. for 24h. Then H₂O (10mL), sat.aq. Na₂S₂O₃ (4mL), and sat. aq. Na₂CO₃ (4mL) were added. The mixture was extracted with CH₂Cl₂ (3×10mL) and the combined organic layer was dried over anhydried Na₂SO₄, filtered, and concentrated under reduced pressure. The residue was purified on silica gel plate (hexane/EtOAc=20/1) to give the yellow oil product of 4-chloroanisole 35mg (90%).

References:

Li, Ting-Ting;Xu, Cui;Xiang, Chang-Bin;Yan, Jie [Chinese Chemical Letters,2013,vol. 24,# 6,p. 535 - 538]