Benzene, 1-(1,1-dimethylethyl)-2-methyl- → 1-(Bromomethyl)-2-(tert-butyl)benzene

HRID 446893Notes

Reaction equation

HRID 446893 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:19])C(=O)C1>CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 33712Benzene, 1-(1,1-dimethylethyl)-2-methyl-HCID 67184N-bromobutanimide

Product 1

HCID 219213581-(Bromomethyl)-2-(tert-butyl)benzeneYield 104.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To 1-tert-butyl-2-methyl-benzene (940 mg, 6.34 mmol), NBS (1.24 g, 1.1 eq) and AIBN (20 mg, catalytic amount) was added CCl4 (12 mL), which was then refluxed for 1 h. The suspended particles were removed by filtration, and washed with CCl4. The organic layers were combined and concentrated under reduced pressure to give 1.5 g of a yellow liquid in a stoichiometric yield.

Workup

  1. temperaturewas then refluxed for 1 h
  2. customThe suspended particles were removed by filtration
  3. washwashed with CCl4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-223a293f774e4a2ab4322c0346a6fa22
Source dataset
uspto-grants-2013_07
Patent number
US08481537B2

Reaction notes

Loading…