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4-bromo-N-(2,2,2-trifluoroethyl)aniline synthesis

6synthesis methods
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Yield:50885-29-5 68%

Reaction Conditions:

Stage #1: 2,2,2-trifluroethylamine hydrochloridewith acetic acid;sodium nitrite in dichloromethane;water at 20; for 0.5 h;
Stage #2: 4-bromo-anilinewith C52H21FeN12O in dichloromethane;water; for 12.5 h;

Steps:

19 Synthesis of 4-bromo-N-(2,2,2-trifluoroethyl)aniline

2 mmol of trifluoroethylamine hydrochloride was added to the reaction tube.1 mL water, 34 uL acetic acid, 1 mL dichloromethane, covered with a rubber stopper,Fixed to the mixer.Take 42 mg of sodium nitrite in a 1.5 mL sample tube.Add 1 mL of water to the sample tube.Shake the sample tube to dissolve sodium nitrite.Dissolving the dissolved sodium nitrite solution into the reaction tube with a syringe,Stir for half an hour at room temperature.Dissolve the iron porphyrin of formula 3 with 1 mL of dichloromethane (R1 = H, R2 = R3 = CN, L = OH) (catalytic amount, primary amine molarAmount of 9/1000), 0.24 mmol of 4-bromoaniline was taken in the sample tube. After half an hour, the mixed solution in the sample tube was dropped into the reaction tube, and stirred while stirring for 12 hours. The reaction solution was cooled to room temperature, and some impurities were removed by filtration, and concentrated and purified by column chromatography to give the desired product. The column chromatography eluent was a mixed solvent of petroleum ether and acetone. The structure of 4-bromo-N-(2,2,2-trifluoroethyl)aniline is as follows:The compound was a pale yellow liquid with a yield of 68%.

References:

CN108997144,2018,A Location in patent:Page/Page column 19-20