Reference of 4863-91-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4863-91-6 name is 3-Chloro-5-fluoroaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
Example 4: Synthesis of Compound 33 33 Compound 33 Compound 33 [099] A flame-dried flask was charged with 2-bromonitrobenzene (50 mg, 0.25 mmol, 1 equiv) tris(dibenzylideneacetone)dipalladium (11.3 mg, 0.0012 mmol, 5 mol%), racemic 2,2′- bis(diphenylphosphino)-l, l’-binaphthyl (11.5 mg, 0.0019 mmol, 7.5 mol%), and cesium carbonate (163.1 mg, 0.50 mmol, 2 equiv). The flask was degassed and purged with nitrogen. Toluene (2.88 mL) was added, followed by 2-chloro-4-fluoroaniline (35.3 mg, 0.25 mmol, 1 equiv). The reaction was heated to 100C with a reflux condenser and stirred for 12 h. The mixture was cooled to room temperature, filtered through a pad of celite, dried over MgS04 and concentrated under reduced pressure. Purification by flash chromatography on silica gel (9: 1 hexanes:ethyl acetate) afforded the desired aniline 33 as an orange solid (58 mg, 88% yield): XH NMR (400 MHz, Acetone-d6) 9.27 (bs, 1H), 8.18 (d, J= 8.5 Hz, 1H), 7.63 (d, J = 8.6 Hz, 1H), 7.52 (d, J = 8.6 Hz, 1H), 7.28 (s, 1H), 7.17 (dt, J= 2.2 Hz, 10.4 Hz, 1H), 7.04 (m, 2H); 13C NMR (100 MHz, Acetone-d6) 164.2 (d, J = 245.7 Hz), 144.0 (d, j = 1 1.8 Hz), 140.9, 136.7, 136.6, 136.2 (d, J= 13.0 Hz), 127.2, 120.7, 1 18.9, 1 18.9, 1 12.0 (d, J= 25.4 Hz), 108.6 (d, J = 24.5 Hz);LCMS (ESI) calc’d for [Ci2H7ClFN202]”([M-H]”): m/z 265.0, found 265.1.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-5-fluoroaniline, and friends who are interested can also refer to it.
Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; BRUICK, Richard, K.; CALDWELL, Charles, G.; FRANTZ, Doug, E.; GARDNER, Kevin, H.; MACMILLAN, John, B.; SCHEUERMANN, Thomas, H.; TAMBAR, Uttam, K.; WO2014/78479; (2014); A2;,
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