Phosphorus tribromide → HCID 22733829, compound

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Reaction Steps

A solution of PBr3 (8.8 g, 32.5 mm) in 100 mL of pyridine was treated with 4-pyrrolidinopyridine (5.0 g, 33.7 mm) over a period of 5 min. The resulting mixture was then stirred at room temperature for 3 days to give the crude 3-dibromophosphino-4-pyrrolidinopyridine (31P NMR: δ152.2 ppm). This compound was used directly for the next step without further purification. Next, polymer-supported secondary amines from Example 1 (9.0 g, 1.1 mmol/g, 9.9 mmol) was slowly added into the mixture above while stirring at room temperature for a period of 10 min. The resulting suspension was refluxed 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 3-P(Br)-4-(NC4H8)C5H3N. 31P NMR (202 MHz, CDCl3): δ168.4 ppm.

Provenance & Evidence