Uses
2,6-Dibromo-1,5-naphthalenediol is a useful synthetic intermediate. It is used to prepare semiconducting polyphenyls and polythiophenes via microwave-assisted Suzuki and Stille cross-coupling reactions. It is also used to prepare and polymerize adamantane or phenylenevinylene or naphthalenevinylene-containing monomers.
Synthesis
Example 17- Synthesis of 2,6-dibromonaphthalene-1,5-diol: 1,5-dihydroxynaphthalene (115.2 g) was suspended in acetonitrile (800 mL) under nitrogen protection. Subsequently, N,N-dimethylformamide (DMF) solution of N-bromosuccinimide (NBS) (400 mL containing 254 g of NBS) was added slowly and dropwise. The reaction mixture was stirred at room temperature and the reaction progress was monitored by gas chromatography-mass spectrometry (GC-MS). Upon completion of the reaction, the reaction was quenched by the addition of water. The resulting precipitate was collected by filtration and washed with plenty of water to give 2,6-dibromonaphthalene-1,5-diol in 80% yield. Mass spectrometry (electrospray ionization, ESI) analysis resulted in a calculated value (C10H6Br2O2) of 317.9614 and a measured value of 317.9.
References
[1] Journal of Organic Chemistry, 2017, vol. 82, # 15, p. 8234 - 8241
[2] Patent: US2011/224445, 2011, A1. Location in patent: Page/Page column 19
[3] Patent: WO2013/149001, 2013, A2. Location in patent: Paragraph 00139
[4] Tetrahedron Letters, 2017, vol. 58, # 40, p. 3854 - 3858
[5] Organic Electronics: physics, materials, applications, 2014, vol. 15, # 12, p. 3558 - 3567
