2-(benzyloxy)-5-broMo-1-trifluoroMethylbenzene

Then, 8.47 g of 4-bromo-2-trifluoromethylphenol, 5.34 g of potassium carbonate, 4.49 g of benzyl chloride and 100 ml of N, N-dimethylformamide were charged into a reaction vessel, and stirred under ice cooling. A round-bottom flask with stirbar was charged with EXAMPLE 49A (1.5 g, 6.22 mmol), Cs2CO3 (6.08 g, 18.67 mmol) and benzyl bromide (0.813 ml, 6.85 mmol) in 15 mL N, N-dimethylformamide. The mixture was stirred at ambient temperature for 16 hours, diluted with water and extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated. The residues were purified by silica gel chromatography eluting with 0-10percent ethyl acetate/hexane, to afford the title compound. MS( ESI(+)) m/e 331.0 (M+H)+.A 100 mL round bottom flask was charged with EXAMPLE 49B (1.9Og, 5.74 mmol), 4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2, 2'-bi(l, 3, 2-dioxaborolane) (1.75g, 6.89 mmol), [l, r-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane (0.234 g, 0.287 mmol), diphenylphosphinoferrocine (0.159g, 0.287 mmol) and potassium acetate (1.689g, 17.21 mmol) in 50 mL dioxane. The mixture was degassed with N2 and heated at 800C overnight, diluted with water, and extracted into ethyl acetate. The organics were washed with brine and dried (MgSO4), filtered, and concentrated. The crude product was purified on silica gel eluting with 0-10percent ethyl acetate/hexane to provide the title compound. MS (DCI(+)) m/e 396 (M+NH4)+; 1H NMR (300 MHz, dimethylsulfoxide- d6) delta ppm 7.64 (dd, 1 H), 7.56-7.16 (m, 7 H), 5.26 (s, 2 H), 1.29 (s, 12 H).Then, 5.10 g of Then, 8.47 g of 4-bromo-2-trifluoromethylphenol, 5.34 g of potassium carbonate, 4.49 g of benzyl chloride and 100 ml of N, N-dimethylformamide were charged into a reaction vessel, and stirred under ice cooling. After 24 hours, the reaction solution was poured into ice-water and extracted three times with 50 ml of diethyl ether. The ether layers were combined, washed with an aqueous 10 percent sodium hydroxide solution, dried over anhydrous magnesium sulfate and then concentrated to give a crude product. This crude product was subjected to silica gel chromatography to give 9.38 g of

Molecular Weight:331.13
XLogP3:5
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:329.98671
Monoisotopic Mass:329.98671
Topological Polar Surface Area:9.2
Heavy Atom Count:19
Complexity:276
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes