Phosphorus tribromide → 4-(Bromomethyl)-3-chloropyridine

HRID 576948Notes

Reaction equation

HRID 576948 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8]O.P(Br)(Br)[Br:11]>C(Cl)(Cl)Cl>[Br:11][CH2:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 12742466(3-Chloropyridin-4-yl)methanol

Product 1

HCID 595894074-(Bromomethyl)-3-chloropyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of (3-chloropyridin-4-yl)methanol (700 mg, 4.9 mmol) in anhydrous chloroform (15 mL) was added dropwise a solution of phosphorus tribromide (460 μL, 4.9 mmol) in anhydrous chloroform (5 mL) at 0° C. The mixture was stirred for 8 hours at room temperature. The solid was filtered and washed with dichloromethane to afford crude 4-(bromomethyl)-3-chloropyridine, which was used for the next step without further purification; 1H NMR (400 MHz, MeOd4): δ 4.95 (s, 2H), 8.21 (d, J=6.0 Hz, 1H), 8.30 (d, J=6.0 Hz, 1H), 9.09 (s, 1H).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with dichloromethane

Sources & evidence

ORD record
ord-51709f8c08e841449a64a31a4fbd7539
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

Loading…