ChemicalBook CAS DataBase List 4-Bromo-3-(trifluoromethyl)aniline

4-Bromo-3-(trifluoromethyl)aniline synthesis

9synthesis methods

Product Name:4-Bromo-3-(trifluoromethyl)aniline
CAS Number:393-36-2
Molecular formula:C7H5BrF3N
Molecular Weight:240.02

98-16-8
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393-36-2
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Yield:393-36-2 92%

Reaction Conditions:

with N-Bromosuccinimide in N,N-dimethyl-formamide at 20; for 3 h;

Steps:

General procedure for the synthesis of 4-Bromo-3-(substituted) aniline (3a-b)
General procedure: To a solution of substituted aniline 2a or 2b in DMF 100 ml was added to a solution of NBS (92 mmol, 1.0 eq) in DMF 100 ml dropwise. The reaction mixture was stirred at room temperature for 3 h, then diluted with ethyl acetate 500 ml and washed with brine 2 x 150 ml. The organic phase was dried Na2SO4, filtered and concentrated to give the title compound 3a or 3b as brownish solid, 90-92 % yield. To a solution of 2a or 2b (0.8 mmol) in the selected solvent (1 ml), a solution of NBS (0.8 mmol) in the same solvent (1 ml) was added batch wise at room temperature, and the reaction was monitored by LC-MS/MS. Mixtures were obtained with traces of dibrominated products. 4-Bromo-3-(trifluoromethyl) aniline (3a) Yield: 92 %; mp 48-50 °C; brownish powder; IR (KBr) ν max: 3485-3362 (N-Hstretch), 2219 (C:N), 1627 (N-Hbend), 1615 1566, 1509, 1467 (C=Carom), 1361, 1185, 1121, 1044 (C-Hbend), 1276, 550 (CF3) cm-1; 1H NMR (CDCl3, 400 MHz, ppm): δ 7.38 (d, 1H, J = 8.8 Hz, C5-H), 6.95 (d, 1H, J = 2.8 Hz, C2-H), 6.63 (dd, 1H, J = 2 Hz, J = 8.4 Hz, C6-H), 3.84 (br s, 2H, -NH2); 13C NMR (100 MHz, CDCl3, ppm): δ 145.7 (C1),135.5 (C5), 130.6 (C3), 124.3 (C6), 121.6 (CF3), 119.07 (C2), 114.1 (C4); HRMS (ESI): m/z calculated for C7H5 79BrF3N [M-H]-: 237.94847; Found: 237.94478; Calculated for C7H5 81BrF3N [M-H]-: 239.94620; Found: 239. 94250.

References:

Elancheran;Saravanan;Choudhury, Bhaswati;Divakar;Kabilan;Ramanathan;Das, Babulal;Devi;Kotoky, Jibon [Medicinal Chemistry Research,2016,vol. 25,# 4,p. 539 - 552]

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367-67-9 Synthesis