3-tert-Butyltoluene → 1-(Bromomethyl)-3-tert-butylbenzene

HRID 446894Notes

Reaction equation

HRID 446894 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:3]=1.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][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:3]=1

Participants

5

Reactant 2

HCID 337113-tert-ButyltolueneHCID 67184N-bromobutanimide

Product 1

HCID 140976451-(Bromomethyl)-3-tert-butylbenzeneYield 101.8%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To 1-methyl-3-tert-butyl-benzene (551 mg, 3.72 mmol), NBS (730 mg, 1.1 eq) and AIBN (14 mg, catalytic amount) was added CCl4 (8 mL), which was then refluxed for 2 h. The suspended particles were removed by filtration, and washed with CCl4. The organic layers were combined and concentrated under reduced pressure to give 860 mg of a yellow liquid (which was identified by NMR to contain about 15% dibromo derivative).

Workup

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

Sources & evidence

ORD record
ord-6bc020a09a1a46ea83300cfad7c5454e
Source dataset
uspto-grants-2013_07
Patent number
US08481537B2

Reaction notes

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