Synthesis
General procedure for the synthesis of 1-bromo-4-dodecylbenzene from 1-(4-bromophenyl)dodecan-1-one: Hydrazine monohydrate (23.6 mL, 4.5 eq.) and potassium hydroxide (24.3 g, 4 eq.) were added to a solution of 1-(4-bromophenyl)dodecan-1-one (36.5 g, 108.87 mmol) in triethylene glycol (180 mL). The reaction mixture was stirred under reflux conditions for about 15 hours. Upon completion of the reaction, the mixture was cooled to room temperature, poured into water, acidified with concentrated hydrochloric acid to pH < 7, and extracted with dichloromethane (3 x 100 mL). The organic phases were combined, washed with water (2 x 50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: 100% pentane) to afford 21.2 g (60% yield, not optimized) of the colorless oily target compound 1-bromo-4-dodecylbenzene. The product was analyzed and confirmed to be consistent with literature data.
References
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[2] Chemistry - A European Journal, 2000, vol. 6, # 23, p. 4327 - 4342
[3] Patent: US2008/267892, 2008, A1. Location in patent: Page/Page column 10
[4] Chemistry - A European Journal, 2017, vol. 23, # 72, p. 18129 - 18133
[5] Journal of Organic Chemistry, 2015, vol. 80, # 19, p. 9401 - 9409
