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ChemicalBook CAS DataBase List 4-BROMO-3-CHLORO-5-(TRIFLUOROMETHYL)ANILINE
914225-58-4

4-BROMO-3-CHLORO-5-(TRIFLUOROMETHYL)ANILINE synthesis

2synthesis methods
69411-05-8 Synthesis
3-AMINO-5-CHLOROBENZOTRIFLUORIDE

69411-05-8
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$15.00/1g

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Yield: 96%

Reaction Conditions:

with N-Bromosuccinimide in dimethyl sulfoxide under 760.051 Torr; for 5.5 h;Inert atmosphere;

Steps:

9 4-bromo-3-chloro-5-(trifluoromethyl)aniline
To a mixture of 3-chloro-5-(trifluoromethyl)aniline (3.25 g, 16.6 mmol, Eq: 1.00) in dimethylsulfoxide (43.4 ml) was added N-bromosuccinimide (3.11 g, 17.4 mmol, Eq: 1.05) in 5 portions over 2.5 hr (622 mg each 30 min). 2h after the last addition, the reaction mixture was partitioned between 10% aqueous sodium sulfite and ethyl acetate. The organic layer was washed with aqueous sat. sodium carbonate, water (3 times) and brine then adsorbed unto silica (6g) and purified on silica gel (column 120 g, Hexane/ethyl acetate 90: 10 to 65:35) to give 4.36 g (96%) of a yellow solid. MS +m/z: 275.8 (M+H)+

References:

F. HOFFMANN-LA ROCHE AG;HOFFMANN-LA ROCHE INC.;PLANCHER, Jean-Marc;WEIKERT, Robert James WO2014/135423, 2014, A1 Location in patent:Page/Page column 39