N-bromobutanimide → 1-(Bromomethyl)-3,5-di-tert-butylbenzene

HRID 1792292Notes

Reaction equation

HRID 1792292 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH3:15])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[C:1]([C:5]1[CH:6]=[C:7]([CH2:15][Br:16])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 848193,5-Bis(tert-butyl)toluene

Product 1

HCID 44475071-(Bromomethyl)-3,5-di-tert-butylbenzeneYield 61.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

3,5-Bis(t-butyl)-1-methylbenzene (200 mg, 0.98 mmol) was dissolved in carbon tetrachloride (4 ml), and then N-bromosuccinimide (192 mg, 1.08 mmol) and AIBN (α,α′-azabisisobutyronitrile) (2 mg) were added thereto. The mixture was heated under reflux and stirred for 5 hours. The filtrate obtained from the filtration of the reaction mixture was evaporated under reduced pressure to give 170 mg (yield: 61%) of a pale yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customThe filtrate obtained from the filtration of the reaction mixture
  4. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-590bd6cc73ae45b885ec4d481e80acdd
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

Loading…