Application of 52807-27-9,Some common heterocyclic compound, 52807-27-9, name is 4-Chloro-2-iodoanisole, molecular formula is C7H6ClIO, 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.
Add 4-chloro-2-iodo-anisole (10.9 mL, 75.0 mmol), trimethylsilyl acetylene (15.9 mL, 112.5 mmol), copper (I) iodide (0.29 g, 1.5 mmol), and THF (225 ML, anhydrous) to a dry round bottom flask. Add diisopropylamine (22.1 mL, 157.5 mmol) and dichlorobis (triphenylphosphine) palladium (II) (1.58 g, 2.3 mmol) and stir the mixture at room temperature under N2 overnight. Quench reaction with water and extract with EtOAc (x2). Wash combined organic layers with brine, dry over MGS04 and concentrate to get 24 g of a black oil. Adsorb on SI02 and purify the residue by flash chromatography on silica gel eluting with 0-3% ETOAC/HEXANES to afford (5-chloro-2-methoxy- phenylethynyl) -trimethylsilane (13.7 g, 76%). Add a solution of potassium hydroxide (3. 28 g, 58. 5 mmol) in water (30 mL) dropwise over 25 minutes to a stirred solution of (5-chloro-2-methoxy-phenylethynyl)- trimethylsilane (13.7 g, 57.4 mmol) in methanol (275 mL) and stir at room temperature for 2 hours. Concentrate, add brine to residue, and extract with EtOAc (x2). Dry organic layer over MGS04 and concentrate to get 13 g of a black oil. Adsorb on Si02 and purify the residue by flash chromatography on silica gel eluting with 0-5% EtOAc/hexanes to afford the title compound (8. 98 g, 94%).
The synthetic route of 52807-27-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ELI LILLY AND COMPANY; WO2005/19184; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com