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

HRID 712645Notes

Reaction equation

HRID 712645 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 then the reaction mixture is directly purified by flash column chromatography give 455 mg of 3-bromo-5-bromomethyl-pyridine.

Workup

  1. customthe reaction mixture is directly purified by flash column chromatography

Sources & evidence

ORD record
ord-f94edaf7e3f940ec97ec851b9df2b0a8
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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