2-AMINO-5-BROMOBENZOPHENONE

Pale Yellow Solid

2-Aminobenzophenone(5 g, 25.35 mmol) was dissolved in 60 ml of dichloromethane and stirred at -10 ° C for 10 min. N-bromosuccinimide (4.74 g, 26.62 mmol) was added portionwise and the reaction mixture After the reaction was carried out for 2 hours, 30 ml of water was added, extracted with methylene chloride and washed with saturated brine. The organic layer was collected and dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography using petroleum ether / Ethyl acetate (ν / ν = 20 / 1-10 / 1) to give 6 g of 2-amino-5-bromobenzophenone as a yellow solid in 86percent.2-amino-benzophenone (5g, 25.35mmol) was dissolved in 60ml of dichloromethane, stirred for 10min at -10 cold trap, was added portionwise N- bromosuccinimide (4.74g, after 26.62mmol), reaction was continued for 2 hours in the cold trap, was added 30ml of water, extracted with dichloromethane, washed with brine, and the organic layer was collected, dried over anhydrous sodium sulfate, the organic solvent was distilled off under reduced pressure, the residue was purified by a silica gel column purified by chromatography, using petroleum ether / ethyl acetate (V / V = 20 / 1-10 / 1)to afford 2-amino-5-bromo-benzophenone 6g, as a yellow solid, a yield of 85.71percentIntermediate 1-a was synthesized according to Reaction Scheme 1 below. In a 1 L round bottom flask reactor, add 2-aminobenzophenone (50 g, 254 mmol) and 500 mL of dimethylformamide. N-Bromosuccinimide (40.6 g, 228 mmol) is added portionwise to the solid. The reaction is terminated by adding excess water. The solid was separated by column chromatography to obtain & lt; intermediate 1-a & gt ;. (52 g, 74percent)To a solution of (2-Amino-phenyl)-phenyl-methanone (5 g, 25 mmol) in DCM (100 mL) is cooled to -10° C., then NBS (4.512 g, 25 mmol) is added in 30 minutes. After the addition the mixture is stirred at -10° C. for 2 h. The mixture is diluted with DCM, washed with salt NaHCO2-aminophenyl)(phenyl)methanone (500 mg) was reacted with KBr, ammonium molbedate, and sodium per borate in AcOH at 0°C for 16 hours to yield (2-amino-5- bromophenyl)(phenyl)methanone (80 mg).Preparation of 2-Amino-5-bromo benzophenone; To a hot (80-100 General procedure: Under a NTo a solution of 5.0 g (19 mmol) of 2-amino-5-bromo-N-methoxy-N-methylbenzamide (4a) in 50 mL of diethyl ether was added 24 mL (48 mmol) of 2 M phenylmagnesium bromide in THF dropwise at 0 °C. The resulting mixture was stirred at 0 °C for 15 min. After quenching with saturated aqueous ammonium chloride solution, the reaction mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. Purification by column chromatography (silica gel, eluting at a gradient of 5-25percent ethyl acetate in hexanes) afforded 3.21 g (60percent) of the title compound as yellow crystals. 2-benzoyl-4-bromoaniline2-benzoyl-4-bromoaniline

(2-Amino-5-bromophenyl)phenyl-methanone is a benzophenone (B204980) derivative that is widely used in the synthesis of pharmaceutical compounds.

Molecular Weight:276.13
XLogP3:3.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:274.99458
Monoisotopic Mass:274.99458
Topological Polar Surface Area:43.1
Heavy Atom Count:16
Complexity:250
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes