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3-Bromo-2,4,5-trimethylaniline synthesis

5synthesis methods
-

Yield:18087-53-1 66%

Reaction Conditions:

with triethylamine hydrochloride;zinc in N,N-dimethyl-formamide at 105;

Steps:

2 Step 2

A suspension of 3-bromo-1,2,4-trimethyl-5-nitrobenzene (63) (3.0 g, 12.5 mmol), zinc dust (3.7 g, 56.1 mmol) and triethylamine HCl (9.4 g, 68.5 mmol) in DMF (42 mL) was heated at 105° C. overnight.
The reaction mixture was allowed to cool to room temperature, and filtered through Celite.
The filtrate was diluted with EtOAc and the organic layer was washed with brine (twice), dried over magnesium sulfate, filtered, and concentrated under reduced pressure.
The crude product was purified by silica gel chromatography (ISCO 24 g silica) and eluted with EtOAc/heptane (0-40%) and gave 3-bromo-2,4,5-trimethylaniline (64) as brown oil which gave a brown solid upon standing (1.8 g, 66% yield). LCMS (ESI) m/z 214, 216 (M+H).

References:

US2019/233440,2019,A1 Location in patent:Paragraph 0268; 0269