Phosphorus tribromide → 4-(Bromomethyl)-3,5-diethylpyridine

HRID 577108Notes

Reaction equation

HRID 577108 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH2:11][CH3:12])[C:8]=1[CH2:9]O)[CH3:2].[Br:13]P(Br)Br>C(Cl)(Cl)Cl>[Br:13][CH2:9][C:8]1[C:3]([CH2:1][CH3:2])=[CH:4][N:5]=[CH:6][C:7]=1[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 59589408(3,5-Diethylpyridin-4-yl)methanol

Product 1

HCID 595893084-(Bromomethyl)-3,5-diethylpyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (3,5-diethylpyridin-4-yl)methanol (1.50 g, 9.07 mmol) in anhydrous chloroform (40 mL) at 0° C. was added dropwise tribromophosphane (2.48 g, 0.861 mL, 9.16 mmol). The reaction mixture was allowed to stir overnight at room temperature. The solvent was evaporated to provide crude 4-(bromomethyl)-3,5-diethylpyridine, which was used for the next step without any further purification; M+ 229.2.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-97ed957f69194f4a95065da5f6690f0a
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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