Uses
10-Bromo-1-decene can be synthesized by reacting 9-decen-1-ol with PBr3. The product undergoes reduction reaction with 2-propylbenzo[d][1,3,2]dioxaborole (PBD) and Bu3SnH under room temperature conditions to yield 1-decene.
Synthesis
General procedure for the synthesis of 10-bromo-1-decene from 9-decen-1-ol: 9-decen-1-ol (10.0 g, 64.1 mmol) and dichloromethane (300 mL) were added to a round bottom flask and the mixture was cooled to 0 °C. Subsequently, triphenylphosphine (21.8 g, 83.1 mmol) and carbon tetrabromide (27.6 g, 83.2 mmol) were added, and the reaction mixture was slowly warmed to room temperature over a period of 1 hr and stirring was continued for 14 hr. After completion of the reaction, purification was carried out by silica gel column chromatography using hexane as eluent. Finally, the solvent was removed under vacuum to afford the target product 10-bromo-1-decene (14.0 g, 63.9 mmol, 100% yield) as a colorless transparent liquid. The spectral data of the obtained product was in agreement with the commercially available standard.
References
[1] Tetrahedron, 2000, vol. 56, # 26, p. 4397 - 4403
[2] Journal of the American Chemical Society, 2012, vol. 134, # 22, p. 9026 - 9029
[3] Synthetic Communications, 2014, vol. 44, # 13, p. 1957 - 1969
[4] Journal of the American Chemical Society, 1998, vol. 120, # 29, p. 7328 - 7336
[5] Organic Letters, 2004, vol. 6, # 19, p. 3333 - 3336
