2-Bromo-3-fluoronitrobenzene

Under mechanical stirring, 94.0 g of water and 102.2 g of concentrated sulfuric acid were slowly added to a 500 mL glass reaction bottle.19.5 g of acetic acid, 19.5 g of 1-fluoro-2-amino-3-nitrobenzene, Concentrated hydrobromic acid 63.2 g (48percent aqueous solution of hydrogen bromide) and cuprous bromide 9.0 g.A solution of 11.2 g of sodium nitrite and 22.4 g of water was added dropwise at room temperature, and the mixture was dripped in about 5 hours.Stirring was continued for 2 hours at room temperature. It was diluted with 130.8 g of water and extracted with 39.0 g of dichloromethane.The oil layer was washed with water 39.0 g, and the solvent was concentrated.get1-fluoro-2-bromo-3-nitrobenzene 23.4 g, yield 85percent.Take In the light of the embodiment 1 1st step operation, changing the reaction conditions in table 1 results.1st step, to the 100 ml reaction flask add phosphate triethyl ester (24.9 g, 150.0 muM), under magnetic stirring state, inserting the bottom-blowing nitrogen 10 minutes, adding 2.82 g (20.0 mmol) of m-fluoronitrobenzene, 9.95 g (30.0 mmol) of carbon tetrabromide and 20.0 g of N, N-dimethylformamide were added to a 250 mL reaction flask, and the mixture was stirred under a magnetic stirring at room temperature. 60.0 mL of Adding lithium t-butoxide tetrahydrofuran solution (132.0 mmol, 2.2 M) was added dropwise for 0.5 h, and the temperature was raised to 60 C for 3 h, and then naturally returned to room temperature. The reaction solution was decomposed by a negative pressure, and 50.0 g of water was added thereto, and 50.0 g of dichloromethane was added for extraction. The oil layer was combined and washed with water (50.0 g × 5). After removing the solvent, the mixture was allowed to stand overnight to obtain a brown solid (2.22 g). Gas chromatography analysis of To a 250 mL reaction flask, 13.2 mL of lithium diisopropylamide (26.4 mmol, 0.5 M) and 50 mL of tetrahydrofuran were added, and the mixture was placed in an ice machine and stirred to cool to -35 C for use. Then, 1.62 g (11.5 mmol) of m-nitrofluorobenzene dissolved in 25 mL of tetrahydrofuran was added dropwise thereto, and the mixture was dropped for 20 minutes, and the temperature of the dropping process was controlled at -35 to -30 C, followed by further heating and stirring for 2.0 hours. Then, 7.46 g (22.9 mmol) of 1, 2-dibromotetrachloroethane dissolved in 25 mL of tetrahydrofuran was added dropwise, and the dropping temperature was controlled at -35 to -30 C, followed by further stirring for 1.0 h. The reaction solution was slowly poured into a 20.0 g beaker containing 10% ammonium chloride solution, stirred for 10 min, quenched by negative pressure, and most of the tetrahydrofuran was distilled off, and then extracted with dichloromethane (50.0 g × 2), and the oil layer was combined. After adding 50.0 g×2 of water, the solvent was removed, and the mixture was allowed to stand overnight to obtain 1.75 g of a yellow solid. Gas chromatography analysis of 2.82 g (20.0 mmol) of m-fluoronitrobenzene, 9.95 g (30.0 mmol) of carbon tetrabromide and 20.0 g of N, N-dimethylformamide were added to a 250 mL reaction flask, and the mixture was stirred under a magnetic stirring at room temperature. 60.0 mL of Adding lithium t-butoxide tetrahydrofuran solution (132.0 mmol, 2.2 M) was added dropwise for 0.5 h, and the temperature was raised to 60 C for 3 h, and then naturally returned to room temperature. The reaction solution was decomposed by a negative pressure, and 50.0 g of water was added thereto, and 50.0 g of dichloromethane was added for extraction. The oil layer was combined and washed with water (50.0 g × 5). After removing the solvent, the mixture was allowed to stand overnight to obtain a brown solid (2.22 g). Gas chromatography analysis of To a 250 mL reaction flask, 13.2 mL of lithium diisopropylamide (26.4 mmol, 0.5 M) and 50 mL of tetrahydrofuran were added, and the mixture was placed in an ice machine and stirred to cool to -35 C for use. Then, 1.62 g (11.5 mmol) of m-nitrofluorobenzene dissolved in 25 mL of tetrahydrofuran was added dropwise thereto, and the mixture was dropped for 20 minutes, and the temperature of the dropping process was controlled at -35 to -30 C, followed by further heating and stirring for 2.0 hours. Then, 7.46 g (22.9 mmol) of 1, 2-dibromotetrachloroethane dissolved in 25 mL of tetrahydrofuran was added dropwise, and the dropping temperature was controlled at -35 to -30 C, followed by further stirring for 1.0 h. The reaction solution was slowly poured into a 20.0 g beaker containing 10% ammonium chloride solution, stirred for 10 min, quenched by negative pressure, and most of the tetrahydrofuran was distilled off, and then extracted with dichloromethane (50.0 g × 2), and the oil layer was combined. After adding 50.0 g×2 of water, the solvent was removed, and the mixture was allowed to stand overnight to obtain 1.75 g of a yellow solid. Gas chromatography analysis of

Molecular Weight:220.00
XLogP3:2.5
Hydrogen Bond Acceptor Count:3
Exact Mass:218.93312
Monoisotopic Mass:218.93312
Topological Polar Surface Area:45.8
Heavy Atom Count:11
Complexity:161
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes