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

HRID 630279Notes

Reaction equation

HRID 630279 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH3:10])[C:7]=1[CH2:8]O.[Br:11]P(Br)Br>ClCCl>[Br:11][CH2:8][C:7]1[C:2]([CH3:1])=[CH:3][N:4]=[CH:5][C:6]=1[CH3:10]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 22663284(3,5-Dimethylpyridin-4-yl)methanol

Product 1

HCID 595894034-(Bromomethyl)-3,5-dimethylpyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3,5-dimethylpyridin-4-yl)methanol (2.55 g, 18.6 mmol) in anhydrous dichloromethane (130 mL) was added tribromophosphane (2.0 mL, 21.1 mmol). The mixture was stirred at room temperature for 5 hours. Dichloromethane was evaporated. The residue was dried in vacuo, affording 4-(bromomethyl)-3,5-dimethylpyridine. The crude product was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-27e741c8862440c69e5bc06f5c084cc6
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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