Carbon tetrabromide → HCID 59455124, compound

Reaction equation

[CH2:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][N:5]=1)[CH2:2][CH3:3].[C:12](Br)(Br)([Br:14])[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:13][C:12]([Br:14])=[CH:8][C:7]1[CH:10]=[CH:11][C:4]([CH2:1][CH2:2][CH3:3])=[N:5][CH:6]=1

Participants

Procedure

6-Propylnicotinaldehyde (0.2 g, 0.00134 mol) was dissolved in DCM (4 mL). Carbon tetrabromide (0.887 g, 0.00268 mol) and triphenylphosphine (1.4 g, 0.00536 mol) were added to the solution followed by stirring at RT overnight. After insoluble matter was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was purified through column chromatography (3% ethylacetate:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch) to provide the desired compound as a yellow colored oil (0.05 g).