Triphenylphosphine → 3-Bromo-5-(bromomethyl)pyridine
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- 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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