5-Bromo-2-fluorobenzotrifluoride

Colorless liquid

To a suspension of copper(II) bromide (7.48 g) in acetonitrile (50 mL) was added 1, 1-dimethylethyl nitrite (5.02 mL) dropwise under ice-cooling, the mixture was stirred under nitrogen for 5 min. A solution of 4-fluoro-3-(trifluoromethyl)aniline (5 g) in acetonitrile was added to the reaction mixture under ice-cooling, the mixture was stirred at room temperature under nitrogen for 2 h. To the resulting suspension was added 1N HCl and the reaction mixture was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate, the combined organic phases were dried over sodium sulphate and concentrated, the residue was purified by column chromatography to give 4-bromo-1-fluoro-2-(trifluoromethyl)benzene (D12) (2 g). δH (CDClComparative Example 4:In a 2000ml three-necked flask, 400g of concentrated sulfuric acid, O-fluorobenzotrifluoride 400g, lithium bromide 20g, ferric bromide 20g, tetrabutylammonium bromide 20g, Bromine 273.17g, control temperature 35-45 , the reaction 6h sampling, GC detection of raw materials 0.36percent.Cooled to below 30 , transferred to 2000ml separation funnel, stationary 1h, the separation of acid, The crude product was put into a 2000 ml bottle, 1000 g of water was added under stirring, and a 10percent sodium hydroxide solution was added dropwise to adjust the pH value to 7 to obtain 550.3 g of 2-fluoro-5-bromobenzotrifluoride crude which was still isolated. The yield was 92.84percent , Containing, 95.9percentProduct by reduced pressure distillation to obtain 517.18g, yield 93.98percent distillation.38A. First, 4-(4-fluoro-3-trifluoromethyl-phenyl)-pyridine 73 was prepared as follows. To a suspension of pyridine-4-boronic acid (2.59 g, 21.1 mmol) in 1-propanol (60 mL) was added A mixture of 2-phenylpyrrolidine (1.46 g, 10 mmol), 4-bromo-1-fluoro-2- (trifluoromethyl) benzene (4.8 g, 20 mmol) and N, N-Diisopropylethylamine (2.5 g, 20 mmol) in Dimethyl sulfoxide (50 mL) was heated to 150C in a sealed tube with stirring overnight. The mixture was cooled and poured into water (100 mL). Then the mixture was extracted with EA (50 mL x 3), the organic was washed with water, brine and dried over anhydrous Na 2SO 4. Solvent was removed in vacuum, the residue was purified by column chromatography with petroleum to give 1- (4-bromo-2- (trifluoromethyl) phenyl) -2-phenylpyrrolidine (180 mg, 4.9 %) as a brown oil.

Molecular Weight:243.00
XLogP3:3.6
Hydrogen Bond Acceptor Count:4
Exact Mass:241.93543
Monoisotopic Mass:241.93543
Heavy Atom Count:12
Complexity:156
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes