Triphenylphosphine → 3-Bromo-5-(bromomethyl)pyridine

HRID 712654Notes

Reaction equation

HRID 712654 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8]O)[CH:5]=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C(=O)N([Br:36])C(=O)C1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][Br:36])[CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 149329483-Bromo-5-(bromomethyl)pyridineYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-Bromo-pyridin-3-yl)-methanol (500 mg, 2.7 mmol) and triphenylphosphine (840 mg, 3.2 mmol) are dissolved in 12 mL of DCM and NBS (570 mg, 3.2 mmol) is added. The mixture is stirred for 4 hrs and the solvent is removed. The residue is purified by flash column chromatography to give 455 mg of 3-bromo-5-bromomethyl-pyridine.

Workup

  1. customthe solvent is removed
  2. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-8c735c7aa67445c19bd2650f637684d3
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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