Phosphorus tribromide → 4-(Bromomethyl)-3-chloro-5-ethylpyridine

HRID 630145Notes

Reaction equation

HRID 630145 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:10][CH3:11])[C:7]=1[CH2:8]O.[Br:12]P(Br)Br>C(Cl)(Cl)Cl>[Br:12][CH2:8][C:7]1[C:6]([CH2:10][CH3:11])=[CH:5][N:4]=[CH:3][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 59589363(3-Chloro-5-ethylpyridin-4-yl)methanol

Product 1

HCID 595893674-(Bromomethyl)-3-chloro-5-ethylpyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (3-chloro-5-ethylpyridin-4-yl)methanol (1.83 g, 10.66 mmol) in anhydrous chloroform (40 mL) was added dropwise tribromophosphane (2.91 g, 1.01 mL, 10.75 mmol) at 0° C. The reaction mixture was allowed to stir overnight at room temperature. The solvent was then evaporated to provide crude 4-(bromomethyl)-3-chloro-5-ethylpyridine, which was used for the next step without any further purification.

Workup

  1. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-d2eaa19f98d047a69413a4a8e7defd6f
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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