Dimethyl-p-toluidine → HCID 21305553, compound

HRID 2084586Notes

Reaction equation

HRID 2084586 reaction equation
[P:1]([Br:4])(Br)[Br:2].[CH3:5][N:6]([CH3:14])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1>N1C=CC=CC=1>[Br:2][P:1]([Br:4])[C:8]1[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:7]=1[N:6]([CH3:14])[CH3:5]

Participants

4

Reactant 2

HCID 7471Dimethyl-p-toluidineHCID 24614Phosphorus tribromide

Product 1

HCID 21305553HCID 21305553, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  1. temperatureThe resulting mixture was then refluxed overnight

Sources & evidence

ORD record
ord-f8ef369e6a33494c81528125ad6cbb08
Source dataset
uspto-grants-2004_04
Patent number
US06716984B2

Reaction notes

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