N-bromobutanimide → 2-Bromomethyl-4-tert-butyl-1-methoxybenzene

HRID 406353Notes

Reaction equation

HRID 406353 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH3:21])[CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:1][CH2:21][C:15]1[CH:14]=[C:13]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:18]=[CH:17][C:16]=1[O:19][CH3:20]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 124222644-Tert-butyl-1-methoxy-2-methylbenzene

Product 1

HCID 666189372-Bromomethyl-4-tert-butyl-1-methoxybenzeneYield 104.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (5.66 g) and 2,2′-azobis(isobutyronitrile) (71 mg) were added to a solution of 4-tert-butyl-1-methoxy-2-methylbenzene (5.16 g) in carbon tetrachloride (25 mL), and the mixture was heated under reflux for 1.5 hours. The reaction solution was ice-cooled and then the insoluble matter was removed by filtration. The filtrate was concentrated under reduced pressure to obtain 7.78 g of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperaturecooled
  4. customthe insoluble matter was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1604004c5f194114a0535c33ef4b5632
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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