Phosphorus tribromide → 3-(Bromomethyl)-5-fluoropyridine hydrobromide

HRID 630023Notes

Reaction equation

HRID 630023 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8]O)[CH:5]=[N:6][CH:7]=1.P(Br)(Br)[Br:11]>ClCCl>[BrH:11].[Br:11][CH2:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 1524495-Fluoro-3-pyridinemethanol

Product 1

HCID 574755023-(Bromomethyl)-5-fluoropyridine hydrobromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-fluoropyridin-3-yl)methanol (430 mg, 3.4 mmol) in anhydrous dichloromethane (30 mL) was added dropwise phosphorus tribromide (650 μL, 6.8 mmol). The mixture was stirred at room temperature overnight. Dichloromethane was evaporated. The residue was dried in vacuo, affording 3-(bromomethyl)-5-fluoropyridine hydrobromide. The product was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-1811b494d4964b0db4b556077bcb297e
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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