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

HRID 630208Notes

Reaction equation

HRID 630208 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-f2e1ff0fd508423db620085c0d8e7fcc
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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