ChemicalBook CAS DataBase List (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone

(2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone synthesis

7synthesis methods

Product Name:(2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone
CAS Number:915095-86-2
Molecular formula:C13H7ClFIO
Molecular Weight:360.55

5-Iodo-2-chlorobenzoic acid (20.0 g, 0.071 mol) was added to a solution of 2.0 M oxalyl chloride in dichloromethane (39 ml, 0.078 mol), stirred for suspension, and then 8 drops of DMF solution was added dropwise. The solution was clarified after the reaction was carried out for 3 hours. The solvent was spin-dried on a rotary evaporator, and then 15 ml of methylene chloride was added. After spin-drying, add 30 ml of dichloromethane, stir, cool to 0-5 ° C, add fluorobenzene (7. lg, 0.074 mol), add anhydrous aluminum trichloride (9.9 g, 0.074 mol) in batches, control The temperature is not more than 5 °C, after the completion of the addition, stirring is continued at 4 ° C for 1 h, the reaction is quenched on the ice-water mixture, the organic phase is separated, and the aqueous phase is extracted with dichloromethane. The phase was washed twice with 1 mol/L hydrochloric acid, once with water, and twice with 1 mol/L NaOH solution. The mixture was washed twice with saturated sodium chloride and dried over anhydrous sodium sulfate. Drain filtration, spin dry solvent to obtain oil after column chromatography, 20. 1g (78.6percent) of a white solid (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone was obtained.

462-06-6
415 suppliers
$10.00/5g

19094-56-5 Synthesis

19094-56-5
524 suppliers
$6.00/5g

(2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone

915095-86-2
224 suppliers
$5.00/250mg

Yield:915095-86-2 94%

Reaction Conditions:

with oxalyl dichloride;N,N-dimethyl-formamide at 25 - 30; for 5 h;

Steps:

1

Example 1 : Synthesis of the fluoride VIII.1Oxalylchloride (176kg; 1386mol; 1 ,14eq) is added to a mixture of 2-chloro-5-iodo benzoic acid (343kg; 1214mol) (compound IX.1 ), fluorobenzene (858kg) and N,N- dimethylformamide (2kg) 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=200mbar). Then the reaction solution (91 1 kg) is added to aluminiumchloride AICI₃ (181 kg) andfluorobenzene (192kg) 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 (1200kg) is separated into two halves (600kg each). From the first half of the organic phase solvent (172kg) is distilled off at a temperature of about 40 to 50°C (p=200mbar). Then 2-propanole (640kg) 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; 40kg) after filtration. Solvent (721 kg) is distilled off at a temperature of about 40 to 50°C and p=200mbar. Then 2-propanole (240kg) is added at a temperature in the range between about 40 to 50°C. If the content of fluorobenzene is greater than 1 % as determined via GC, another 140kg of solvent are distilled off and 2-propanole (140kg) is added. Then the solution is cooled from about 50°C to 40°C within one hour and seeding crystals (50g) are added. The solution is further cooled from about 40°C to 20°C within 2 hours. Water (450kg) 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 ; 800kg). The product is dried until a water level of <0.06%w/w is obtained. The second half of the organic phase is processed identically. A total of 410kg (94%yield) of product which has a white to off-white crystalline appearance, is obtained. The identity of the product is determined via infrared spectrometry.

References:

WO2011/39107,2011,A1 Location in patent:Page/Page column 18-19