2-BROMOBENZOPHENONE

White solid

General procedure: In an oven dried Schlenk tube, were added alcohol 1 (69.0–199.5 mg, 0.5 mmol), CuI (10 molpercent)and 1, 10-Phenanthroline (20 molpercent) and K3PO4 (2 mmol) followed by the addition of dioxane (2mL) at room temperature under open air atmosphere. The stirred reaction mixture was heated inan oil bath at 80 C for 7–48 h. Progress of the reaction was monitored by TLC till the reaction iscompleted. Then, the reaction mixture was cooled to room temperature, quenched with aqueousNH4Cl solution and then extracted with CH2Cl2 (3 10 mL). The organic layer was washed withsaturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent under reducedpressure and purification of the crude material by silica gel column chromatography (petroleumether/ethyl acetate) furnished the aldehyde/ketone 2 (61–97percent).General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdClGeneral procedure: A 5 mL flask charged with benzoyl chloride (1.0 mmol), arylboronic acid (0.5 mmol), K2CO3 (1.0 mmol), complex 1 (0.5 molpercent, 3.1 mg), PPh3 (0.01 mmol, 1.3 mg) and toluene (2.0mL) was put into a preheated 70 oC oil bath for an appropriate period of time under air. After thereaction was finished, the reaction mixture was cooled to room temperature, filtered through ashort silica column and washed with ethyl acetate. Then the combined filtrates were concentratedin vacuo and the residue was purified by flash chromatography (eluent: ethylacetate/petroleumether). All the products were known compounds and characterized by comparing mp, 1H NMRand 13C NMR spectra with literature.General procedure: A reaction vessel was charged with a mixture of phenylboronic acid (0.5 mmol), K2-Bromo-benzoic acid (21g, 100mmol) was dissolved in thionyl chloride was heated at reflux for 1h, the spin off the excess thionyl chloride, to give 2-bromobenzoyl chloride; followed by 2-bromo-benzoyl chloride 50ml chloroform was added and after drying anhydrous aluminum (16g, 120mmol), stirred for 15min at room temperature was added dropwise benzene (9.4g, 11ml, 120mmol) in dry chloroform solution, stirred at room temperature 4h, poured slowly into ice-hydrochloric acid aqueous solution, CHGeneral procedure: Thiolester (0.25 mmol), arylboronic acids (0.375 mmol), CuI (20 molpercent, 10 mg), Ag2CO3 (5 molpercent, 4 mg) and DMF (3 ml) were taken in a 25 ml round bottomed flask. The reaction mixture was heated at 120 C for 8–24 h. The reaction monitored using TLC. Upon completion, the reaction mixture was diluted with water and extracted with DCM (3x10 ml). The combined organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The resulting ketone was purified was purified using silica gel column chromatography (EtOAc and petroleum ether 60–80 C).General procedure: In around-bottom flask, diarylmethanes (1.0 mmol), NBS (889.9 mg, 5.0 mmol) andwater (0 or 5.0 mmol) were dissolved in CHClGeneral procedure: Under a nitrogen atmosphere 2-bromo-Nmethoxy-N-methylbenzamide (10) (about 1 mmol) was dissolved in anhydrous THF (3 mL). The solution was cooled to 0 °C and the appropriate Grignard reagent (3.0 equiv) was added. The mixture was stirred for 15 h, then 2M hydrochloric acid (10 mL) was added and extracted with ethyl acetate (3*15 mL). The combined organic layers were dried over MgSOPreparation of (2-bromophenyl)(phenyl)methanone 2ka:; A dry and argon flushed 10 mL flask, equipped with a magnetic stirrer and a septum, was charged with i-PrMgCl*LiCl (1 mL, 1.05 M in THF, 1.05 mmole), the reaction mixture was cooled to -15°C and 1, 2-dibromobenzene (235.9 mg, 1 mmole) was then added dropwise. The Br/Mg-exchange was complete after 1.5 h (checked by GC analysis of reaction aliquots, conversion more than 98percent) and solution of CuCN*2LiCl (0.1 mL, 1.0 M in THF, 0.1 mmole) was added. After stirring for 10 min at -15°C benzoyl chloride (140.6 mg, 1 mmole) was added. The reaction mixture was stirred for 1 h at -15°C and was then quenched with sat. NH4Cl solution (2 mL) and also 5 drops of concentrated NH3 was added. The aqueous phase was extracted with ether (3 x 4 mL) and the organic fractions were washed with brine (5 mL), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by flash chromatography (dichloromethane) yielding the ketone (2ka) as a white cristals (219.3 mg, 84 percent). 1H-NMR (CDCl3, 200 MHz):δ = 7.86-7.78 (m, 2 H); 7.68 - 7.56 (m, 2 H); 7.52 - 7.30 (m, 5 H).

Molecular Weight:261.11
XLogP3:4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:259.98368
Monoisotopic Mass:259.98368
Topological Polar Surface Area:17.1
Heavy Atom Count:15
Complexity:221
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes