Phosphorus tribromide → 4-(Bromomethyl)-3-chloropyridine hydrobromide

HRID 577254Notes

Reaction equation

HRID 577254 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8]O.[Br:10]P(Br)Br>ClCCl>[BrH:10].[Br:10][CH2:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 12742466(3-Chloropyridin-4-yl)methanol

Product 1

HCID 668153214-(Bromomethyl)-3-chloropyridine hydrobromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-chloropyridin-4-yl)methanol (1.0 g, 7.2 mmol) in anhydrous dichloromethane (35 mL) was added dropwise tribromophosphane (750 uL, 7.9 mmol). The mixture was stirred at room temperature for 5 hours. Dichloromethane was evaporated, and the residue was dried in vacuo, affording 4-(bromomethyl)-3-chloropyridine hydrobromide. The product was used for the next step without further purification.

Workup

  1. customDichloromethane was evaporated
  2. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-9b54ac502edb48ba98e40588140f14de
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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