Dimethyl-p-toluidine → HCID 21305553, compound

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Reaction Steps

A solution of PBr3 (7.0 g, 26.0 mm) in 80 mL of pyridine was treated with N,N-dimethyl-p-toluidine (10.0 g, 74.0 mm) over a period of 5 min. The resulting mixture was then refluxed overnight. to give the crude 2-dibromophosphino-N,N-dimethyl-p-toluidine (31P NMR: δ149.1 ppm). This compound was used directly for the next step without further purification. Next, polymer-supported secondary amines prepared as in Example 1 (10.0 g, 1.06 mmol/g, 10.6 mmol) was slowly added into the mixture above while stirring at room temperature for a period of 10 min. The resulting suspension was stirred at room temperature overnight before the solution was filtered off. The resin was washed with THF (2×50 mL), hexane (3×50 mL), CH2Cl2 (4×50 mL), and hexane (2×50 mL). The resulting resin was dried in vacuum overnight to yield the polymer-supported 2-P(Br)-1-NMe2-4-(Me)C6H3 31P NMR (122 MHz, CDCl3): δ157.0 ppm.

Provenance & Evidence