19094-56-5, name is 2-Chloro-5-iodobenzoic acid, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C7H4ClIO2
Oxalylchloride (176 kg; 1386 mol; 1.14 eq) is added to a mixture of 2-chloro-5-iodo benzoic acid (343 kg; 1214 mol) (compound IX.1), fluorobenzene (858 kg) and N,N-dimethylformamide (2 kg) within 3 hours at a temperature in the range from about 25 to 30° C. (gas formation). After completion of the addition, the reaction mixture is stirred for additional 2 hours at a temperature of about 25 to 30° C. The solvent (291 kg) is distilled off at a temperature between 40 and 45° C. (p=200 mbar). Then the reaction solution (911 kg) is added to aluminiumchloride AlCl3 (181 kg) and fluorobenzene (192 kg) at a temperature between about 25 and 30° C. within 2 hours. The reaction solution is stirred at the same temperature for about an additional hour. Then the reaction mixture is added to an amount of 570 kg of water within about 2 hours at a temperature between about 20 and 30° C. and stirred for an additional hour. After phase separation the organic phase (1200 kg) is separated into two halves (600 kg each). From the first half of the organic phase solvent (172 kg) is distilled off at a temperature of about 40 to 50° C. (p=200 mbar). Then 2-propanole (640 kg) is added. The solution is heated to about 50° C. and then filtered through a charcoal cartouche (clear filtration). The cartouche may be exchanged during filtration and washed with a fluorobenzene/2-propanole mixture (1:4; 40 kg) after filtration. Solvent (721 kg) is distilled off at a temperature of about 40 to 50° C. and p=200 mbar. Then 2-propanole (240 kg) is added at a temperature in the range between about 40 to 50° C. If the content of fluorobenzene is greater than 1percent as determined via GC, another 140 kg of solvent are distilled off and 2-propanole (140 kg) is added. Then the solution is cooled from about 50° C. to 40° C. within one hour and seeding crystals (50 g) are added. The solution is further cooled from about 40° C. to 20° C. within 2 hours. Water (450 kg) is added at about 20° C. within 1 hour and the suspension is stirred at about 20° C. for an additional hour before the suspension is filtered. The filter cake is washed with 2-propanole/water (1:1; 800 kg). The product is dried until a water level of <0.06percent w/w is obtained. The second half of the organic phase is processed identically. A total of 410 kg (94percent yield) of product which has a white to off-white crystalline appearance, is obtained. The identity of the product is determined via infrared spectrometry.
The synthetic route of 19094-56-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/237789; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com