Phosphorus tribromide → 4-(Bromomethyl)-3,5-dichloropyridine hydrobromide
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
Product 1
Reagents, catalysts & solvents 1
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
- customDichloromethane was evaporated
- 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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