Acetonitrile → 1,3,5-Tricyclohexylbromobenzene

Reaction equation

[Br:1]N1C(=O)CCC1=O.C(#N)C.[CH:12]1([C:18]2[CH:23]=[C:22]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:21]=[C:20]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:19]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl>[Br:1][C:19]1[C:20]([CH:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)=[CH:21][C:22]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:23][C:18]=1[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Procedure

A 500-mL three-neck flask was charged with 15.7 g of N-bromosuccinimide and 100 g of acetonitrile. Under ice cooling, a dilute solution of 28.4 g of 1,3,5-tricyclohexylbenzene (prepared by known reaction) in 60 g of methylene chloride was added dropwise over 30 minutes. The solution was warmed to room temperature and aged for 12 hours. The resulting crystal precipitate was filtered, washed with acetonitrile and water, and dried, obtaining the target compound, 2-bromo-1,3,5-tricyclohexylbenzene as white crystal. Amount 28.4 g, yield 81%.