N,N'-Dimethylethylenediamine → n-(2,4-Difluorophenyl)-n,n'-dimethylethylene-1,2-diamine

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Reaction Steps

Combine 1-bromo-2,4-difluorobenzene (1.00 g, 5.18 mmol), N,N′-dimethyl-ethylenediamine (2.74 g, 31.1 mmol), NaO-t-Bu (0.70 g, 7.2 mmol), Pd(dba)2 (0.060 g, 0.10 mmol) and (±)-BINAP (0.19 g, 0.31 mmol) in toluene (10 ml). Heat at 110° for 18 h, allow to cool, and extract with 1N HCl. Basify the aqueous solution with NaOH and extract with CH2Cl2. Dry, concentrate, and purify by PLC to give N-(2,4-difluoro-phenyl)-N,N′-dimethylethylenediamine.

Provenance & Evidence