4-BROMO-5-FLUORO-2-METHYLANILINE synthesis
- Product Name:4-BROMO-5-FLUORO-2-METHYLANILINE
- CAS Number:52723-82-7
- Molecular formula:C7H7BrFN
- Molecular Weight:204.04
367-29-3
52723-82-7
General procedure for the synthesis of 4-bromo-5-fluoro-2-methylaniline from 5-fluoro-2-methylaniline: In a dry reaction flask, N-bromosuccinimide (NBS, 14.22 g, 80 mmol), 5-fluoro-2-methylaniline (10 g, 80 mmol), and N,N-dimethylformamide (DMF, 200 mL) were added in sequence. The reaction mixture was stirred at 25°C for 12 hours. Upon completion of the reaction, the mixture was slowly poured into ice water and a solid was precipitated. The solid was collected by filtration and washed with cold water to afford 4-bromo-5-fluoro-2-methylaniline (13 g, 71% yield) as a yellow solid. Product mass spectral data: LC-MS m/z 204 ([M + H]+), retention time 1.68 min.
367-29-3
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Yield: 71%
Reaction Conditions:
with N-Bromosuccinimide in N,N-dimethyl-formamide at 25; for 12 h;
Steps:
4-Bromo-5-fluoro-2-methylaniline
A mixture of NBS (14.22 g, 80 mmol), 5-fluoro-2-methylaniline (10 g, 80 mmol) and N,Ndimethylformamide (200 mL) was stirred at 2500 for 12 h. The mixture was then poured into water and the solid was filtered to afford the title compound (13 g, 71 % yield) as yellow solid. L0-MS m/z 204 (M+H), 1 .68 mm (ret. time).
References:
GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED;ASTEX THERAPEUTICS LIMITED;KERNS, Jeffrey K.;YAN, Hongxing;CALLAHAN, James Francis;HEIGHTMAN, Thomas Daniel;BOEHM, Jeffrey Charles;WOOLFORD, Alison Jo-Anne WO2016/203401, 2016, A1 Location in patent:Page/Page column 72
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