Benzoyl Peroxide → 1-(Bromocyclohexyl)-4-nitrobenzene

HRID 1633926Notes

Reaction equation

HRID 1633926 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[Br:16][C:1]1([C:7]2[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 795641-Cyclohexyl-4-nitrobenzene

Product 1

HCID 225017731-(Bromocyclohexyl)-4-nitrobenzeneYield 58.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

4-Cyclohexylnitrobenzene (22.6 g, 0.11 mol) and N-bromosuccinimide (21.6 g, 0.12 mol) were suspended in tetrachloromethane (200 mL) and a catalytic amount of dibenzoylperoxide was added. The reaction mixture was stirred at 80° C. for 4.5 hours. The reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate (400 mL) and washed with water (100 mL). The aqueous phase was extracted with ethyl acetate (200 mL) and the combined organic phases were washed with water (3×150 mL), dried over MgSO4 and concentrated in vacuo. The residue was crystallised from ethyl acetate and heptane to give 18.4 g of 1-(bromocyclohexyl)-4-nitrobenzene.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate (400 mL)
  3. washwashed with water (100 mL)
  4. extractionThe aqueous phase was extracted with ethyl acetate (200 mL)
  5. washthe combined organic phases were washed with water (3×150 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallised from ethyl acetate and heptane

Sources & evidence

ORD record
ord-5ea89f07d9fd4d408cdbdf06efc41992
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

Loading…