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

HRID 576939Notes

Reaction equation

HRID 576939 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH2:8]O.P(Br)(Br)[Br:12]>C(Cl)(Cl)Cl>[Br:12][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 222277664-(Bromomethyl)-3,5-dichloropyridineYield 75.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of (3,5-dichloropyridin-4-yl)methanol (470 mg, 2.6 mmol) in anhydrous chloroform (10 mL) was added dropwise a solution of phosphorus tribromide (250 μL, 2.6 mmol) in anhydrous chloroform (2 mL) at 0° C. The mixture was stirred for 1.5 hours at room temperature. The solid was filtered and washed with dichloromethane to afford 4-(bromomethyl)-3,5-dichloropyridine (471 mg, 75% yield), which was used for next step without further purification; 1H NMR (400 MHz, MeOD4): δ 4.76 (s, 2H), 8.63 (s, 2H).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with dichloromethane

Sources & evidence

ORD record
ord-0c6bddd4b1794f2586cfe38cc814d812
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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