Acetonitrile → 1,3,5-Tricyclohexylbromobenzene

HRID 529866Notes

Reaction equation

HRID 529866 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

5

Reactant 3

HCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 149640301,3,5-Tricyclohexylbenzene

Product 1

HCID 670505411,3,5-TricyclohexylbromobenzeneYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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%.

Workup

  1. filtrationThe resulting crystal precipitate was filtered
  2. washwashed with acetonitrile and water
  3. customdried

Sources & evidence

ORD record
ord-4c283bd0990c4ba4b53ff52b26afb118
Source dataset
uspto-grants-2016_05
Patent number
US09348227B2

Reaction notes

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