Carbon tetrabromide → 2-Bromo-6-(1-bromo-2-fluoroethyl)pyridine
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8](O)[CH2:9][F:10])[CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:8]([Br:32])[CH2:9][F:10])[N:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1-(6-Bromopyridin-2-yl)-2-fluoroethanol (0.525 g, 2.39 mmol) and triphenylphosphine (1.252 g, 4.77 mmol) were taken up in DCM (25 mL). A solution of carbon tetrabromide (1.582 g, 4.77 mmol) in DCM (10 mL) was added and the resulting mixture stirred at room temperature overnight. The precipitate was removed by filtration and the filtrate concentrated in vacuo. Purification of the residue by silica gel column chromatography (0-10% EtOAc-hexanes) gave the title compound as a colorless oil.