ChemicalBook CAS DataBase List (5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone

(5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone synthesis

10synthesis methods

Product Name:(5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone
CAS Number:461432-22-4
Molecular formula:C15H12BrClO2
Molecular Weight:339.61

21900-52-7

103-73-1

(5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone

461432-22-4

Under the protection of nitrogen, 2.1 g of tert-butyldimethylchlorosilane prepared in step 1) was mixed with 5-bromo-2-chlorobenzoyl chloride in anhydrous dichloromethane and stirred for 30 min at 0 to 10 °C. Subsequently, 1.2 mol of phenethyl ether and 1.1 mol of ferric chloride were sequentially added to the reaction system, and the reaction temperature was maintained at 14.7 °C, and the reaction continued to be stirred for 5 hours. After completion of the reaction, the reaction mixture was quenched by pouring it into ice water, extracted with dichloromethane, the organic phase was washed with water, and 31 g of 5-bromo-2-chloro-4'-ethoxy benzophenone (intermediate of dagliflozin) was obtained after concentration in 91.4% yield and 99.49% purity.

21739-92-4 Synthesis

21739-92-4
686 suppliers
$8.00/10g

103-73-1 Synthesis

103-73-1
360 suppliers
$8.00/25g

461432-22-4
350 suppliers
$5.00/250mg

Yield:461432-22-4 178 g

Reaction Conditions:

Stage #1:5-bromo-2-chlorobenzoic acid with thionyl chloride;N,N-dimethyl-formamide in dichloromethane at 25 - 40; for 4 h;
Stage #2: with aluminum (III) chloride in dichloromethane at 5 - 30; for 0.166667 h;
Stage #3:Phenetole in dichloromethane at 25 - 30; for 10 h;

Steps:

1 Preparation of (5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone (Formula-3)
Thionyl chloride (194.78 ml) was slowly added to a mixture of 5-bromo-2-chlorobenzoic acid compound of formula-2 (200 gms), dichloromethane (1000 ml) and dimethylformamide (1 ml) at 25-30° C.
Heated the reaction mixture to 35-40° C. and stirred for 4 hrs at the same temperature.
Distilled off the solvent completely from the reaction mixture under reduced pressure.
Dichloromethane (1600 ml) was added to the obtained compound at 25-30° C. and stirred for 20 mins at the same temperature.
Cooled the reaction mixture to 5-10° C. and stirred for 15 mins at the same temperature.
Aluminium chloride (110.9 gms) was slowly added to the reaction mixture at 5-10° C., the temperature of the reaction mixture was raised to 25-30° C. and stirred for 10 mins at the same temperature.
Phenetole (103.5 gms) was slowly added to the reaction mixture at 25-30° C. and stirred for 10 hrs at the same temperature.
The reaction mixture was poured into chilled hydrochloric acid solution (1000 ml of hydrochloric acid in 1000 gms of ice) at 25-30° C. and stirred for 20 mins at the same temperature.
Separated the both organic and aqueous layers, the organic layer was washed with 5% aqueous sodium bicarbonate solution followed by with 10% aqueous sodium chloride solution.
Distilled off the solvent completely from the organic layer under reduced pressure.
Methanol (400 ml) was added to the obtained compound at 55-60° C. and stirred for 45 mins.
Cooled the reaction mixture to 0-5° C. and stirred for 2 hrs at the same temperature.
Filtered the precipitated solid, washed with methanol.
Methanol (500 ml) was added to the wet solid, heated to 65-70° C. and stirred for 1 hr 30 mins at the same temperature.
Cooled the reaction mixture to 25-30° C., then to 0-5° C. and stirred for 3 hrs at 0-5° C.
Filtered the precipitated solid, washed with methanol and then dried to get title compound.
Yield: 178 gms; Melting range: 68-72° C.; Purity by HPLC: 98.8%.