3'-CHLORO-2,2,2-TRIFLUOROACETOPHENONE

General procedure: Method A: a mixture of 2, 2, 2-trifluoro-1-(4-methoxyphenyl)ethanol (2c) (0.206 g, 1.0 mmol) and sodium 2-iodobenzenesulfonate (8) (as monohydrate, 0.016 g, 0.05 mmol, 5 molpercent), powdered OxoneAccurate weighing of m-chlorobromobenzene (3-chlorobromobenzene) (19.15 g, 0.1 mol) was dissolved in 100 ml of tetrahydrofuran and the ethanol-dry ice bath cooled the solution temperature to a negative 78 to negative 50 ° C. A solution of butyllithium (0.12 mol) was added dropwise and incubated for 1 hour at a negative 78 to negative temperature of 50 ° C. Then, ethyl trifluoroacetate (18.4 g, 0.13 mol) was added dropwise at this temperature. After completion of the dropwise addition, the mixture was withdrawn and the mixture was spontaneously stirred at room temperature. Then, hydrochloric acid (30 ml, 0.3 mol) was added dropwise, the layers were stirred, the organic layer was depressurized to remove the solvent. 20.7 g of crude 2, 2, 2-trifluoro-(3'-chlorophenyl)ethanone was obtained and distilled to give 20.3 g of a colorless transparent liquid, content of 95percent, yield 97.3percent.Accurate weighing of m-chloroiodobenzene (3-chloroiodobenzene) (23.85 g, 0.1 mol) was dissolved in 120 ml of methyl tert-butyl ether and the ethanol cooled ice bath cooled to a negative temperature of 20 to minus 10 ° C. A solution of isopropylmagnesium chloride (0.13 mol) was added dropwise and incubated for 1 hour at a negative 20 to minus 10 ° C after completion of the dropwise addition. Then, trifluoroacetate (18.4 g, 0.13 mol) was added dropwise at this temperature. After completion of the dropwise addition, the mixture was stirred and cooled to room temperature, and then hydrochloric acid (30 ml, 0.3 mol) was added dropwise. The organic layer was removed under reduced pressure to give 20.5 g of crude 2, 2, 2-trifluoro-(3'-chlorophenyl)ethanone and distilled to give 18.3 g of a colorless transparent liquid, content of 95.9.7percent, the yield of 88percent.The flask was added with magnesium powder (3 g, 0.125 mol), 20 ml of tetrahydrofuran, stirred. Accurately weighed m-dichlorobenzene (14.7 g, 0.1 mol) was dissolved in an additional 30 ml of tetrahydrofuran and added to a constant pressure dropping funnel, and 10percent of the m-dichlorobenzene solution was added to the flask. The flask was heated to 40-45 ° C and then 0.3 ml of 1, 2-dibromoethane was added to initiate the reaction. Then, the m-dichlorobenzene solution was slowly added dropwise at this temperature. After completion of the dropwise addition, the mixture was stirred at 40 to 50 ° C for 2 hours, and then the inside of the flask was cooled to 10 to 30 ° C, and trifluoroacetyl diethylamine was added dropwise, and the mixture was stirred for 30 minutes. Then, hydrochloric acid (30 ml, 0.3 mol) was added and the layers were separated and the organic layer was removed under reduced pressure to give 20.8 g of crude product. After distillation, 17.4 g of colorless transparent 2, 2, 2-trifluoro-(3'-chlorophenyl)ethanone was obtained, the content was 99.3percent and the yield was 83.4percent.

Molecular Weight:208.56
XLogP3:3.6
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:207.9902769
Monoisotopic Mass:207.9902769
Topological Polar Surface Area:17.1
Heavy Atom Count:13
Complexity:202
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes