Uses
1-Bromo-4-fluoronaphthalene is the starting material for the synthesis of Fluorobenzo[c]fluoren (F588435) which is a polycyclic aromatic hydrocarbon used in materials science extensively due to utility in organic electronics, light emitting diodes and solar cells.
Synthesis
General procedure for the synthesis of 1-bromo-4-fluoronaphthalene from 1-fluoronaphthalene: 1-fluoronaphthalene (20.0 g, 0.137 mol) was added to a 500 mL single-necked flask with carbon tetrachloride (120.0 mL), and bromine (10.9 g, 0.068 mol) was added dropwise slowly, followed by heating and refluxing for 2 hours. Upon completion of the reaction, the reaction solution was concentrated under reduced pressure and then the concentrate was poured into methanol (80.0 mL). The solid was allowed to precipitate overnight at room temperature to give 28.2 g of 1-bromo-4-fluoronaphthalene in 91.5% yield.
References
[1] Patent: CN106478376, 2017, A. Location in patent: Paragraph 0009; 0020; 0021; 0029; 0030; 0038; 0039; 0047
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 6, p. 1575 - 1586
[3] Justus Liebigs Annalen der Chemie, 1931, vol. 487, p. 270,282
[4] Patent: US2001/49379, 2001, A1
[5] Patent: US6211208, 2001, B1
