Phosphorus tribromide → 4-(Bromomethyl)-3,5-dichloropyridine hydrobromide

HRID 577166Notes

Reaction equation

HRID 577166 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH2:8]O.[Br:11]P(Br)Br>ClCCl>[BrH:11].[Br:11][CH2:8][C:7]1[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=1[Cl:10]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 17855219(3,5-Dichloropyridin-4-yl)methanol

Product 1

HCID 668153104-(Bromomethyl)-3,5-dichloropyridine hydrobromideYield 156.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3,5-dichloropyridin-4-yl)methanol (1.9 g, 10.7 mmol) in anhydrous dichloromethane (75 mL) was added tribromophosphane (1.1 mL, 11.5 mmol). The mixture was stirred at room temperature for 1.5 hours. Dichloromethane was evaporated, and the mixture was co-evaporated with toluene (2×20 mL). The residue was dried in vacuo, affording 4-(bromomethyl)-3,5-dichloropyridine hydrobromide (2.9 g, 98% yield), which was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-be2afbcb2c7a459583b1be10f1ac457a
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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