3-Bromo-5-fluorobenzonitrile

off-white crystalline

3-Bromo-5-fhiorobenzonitrileA 250-mL round-bottom flask equipped with a magnetic stir bar was charged with 1, 3- dibromo-5-fluorobenzene (7.70 g, 30.3 mmol), DMF (45 mL), pyridine (4.9 mL), and copper (I) cyanide (2.72 g, 30.3 mmol) under nitrogen. A reflux condenser was attached to the flask. The green, cloudy mixture was stirred at reflux for 3 h. Once lower Rf impurities were observed, the reaction was allowed to cool to room temperature. The reaction was quenched with 30 mL of ether, and a precipitate formed in the dark solution. The precipitate was gravity- filtered though Celite. The filtrate was rinsed thee times with ether (100 mL/50 g bromide). The isolated solution was added to a separatory funnel. The organic layer was washed with a 2:1 mixture of water and concentrated ammonium hydroxide (30 mL), followed by saturated ammonium chloride solution (2 x 30 mL) and saturated sodium bicarbonate (30 mL). The aqueous layers were extracted with ether (3 x 40 mL). The organic layers were combined and dried over anhydrous sodium sulfate. The product was purified by flash column chomatography to yield 3-bromo-5-fluorobenzonitrile (2.1O g, 35percent). A mixture of 1, 3-dibromo-5-fluorobenzene (7.4 g, 29.3 mmol), copper(I) cyanide (2.6 g, 29.3 mmol), pyridine (3 mL) and N, N-dimethylformamide (30 mL) under an argon atmosphere was heated to 150 °C for 4.5 h. Mixture was allowed to room temperature, diethyl ether (100 mL) was added and the formed precipitate was removed via filtration, the precipitate was washed with diethyl ether (100 mL), the filtrate was washed consecutively with: 1) 10 percent ammonium hydroxide (100 mL), 2) saturated ammonium chloride (100 mL), and 3) saturated sodium bicarbonate (100 mL), dried over magnesium sulfate and evaporated. Purification of the residue by flash chromatography, using a stepwise gradient of heptane to heptane:ethyl acetate 9:1 afforded the title compound (1.3 g, 23percent). 3-Bromo-5-fluorobenzonitrile 3-Bromo-5-fluorobenzonitrile EXAMPLE 171 3-Bromo-5-fluorobenzonitrile. Example 17

Molecular Weight:200.01
XLogP3:2.4
Hydrogen Bond Acceptor Count:2
Exact Mass:198.94329
Monoisotopic Mass:198.94329
Topological Polar Surface Area:23.8
Heavy Atom Count:10
Complexity:162
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes