2,6-Dibromotoluene → 1,3-Dibromo-2-(bromomethyl)benzene

HRID 2069746Notes

Reaction equation

HRID 2069746 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH3:9].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH2:9][Br:10]

Participants

5

Reactant 2

HCID 346812,6-DibromotolueneHCID 67184N-bromobutanimide

Product 1

HCID 133810151,3-Dibromo-2-(bromomethyl)benzeneYield 107%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

2,6-dibromotoluene (2.50 g, 10.0 mmol) was dissolved in 20 mL carbontetrachloride. N-bromosuccinimide (1.87 g, 10.5 mmol) was added followed by benzoyl peroxide (73 mg, 0.30 mmol). The resulting mixture was heated at reflux for 90 minutes. 50 mL petroleum ether was added. This was filtered and concentrated in vacuo to yield 1,3-Dibromo-2-bromomethyl-benzene (3.52 g, 10.7 mmol). 1HNMR (300 MHz, CDCl3) δ 4.83 (s, 3H), 7.02 (t, J=8 Hz, 1H), and 7.55 (d, J=8 Hz, 2H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 90 minutes
  3. filtrationThis was filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d222f2833c584dd9962072810918b54a
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

Loading…