Benzoyl Peroxide → HCID 19046452, compound

HRID 1439938Notes

Reaction equation

HRID 1439938 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH3:12])[CH:8]=[C:9]([Cl:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[CH2:12][Br:13])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 190464341-tert-Butyl-3-chloro-5-methylbenzene

Product 1

HCID 19046452HCID 19046452, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-t-Butyl-5-chlorotoluene (5.7 g) was dissolved in carbon tetrachloride (80 ml) and N-bromosuccinimide (5.56 g) was added followed by benzoyl peroxide (750 mg). This mixture was heated at reflux for 6 h. The mixture was cooled, filtered through celite and the flitrate was concentrated in vacuo. The residue was purified by chromatography on silica using hexane as eluant. This afforded the title compound as a colourless liquid. 1H NMR (360 MHz, CDCl3) δ 1.31 (9H, s, (CH3)3), 4.42 (2H, s, CH2), 7.20 (1H, t, J=1.5 Hz, ArH), 7.26 (1H, t, J=1.5 Hz, ArH), 7.28 (1H, t, J=1.5 Hz, ArH).

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for 6 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through celite
  5. concentrationthe flitrate was concentrated in vacuo
  6. customThe residue was purified by chromatography on silica

Sources & evidence

ORD record
ord-358a5873c602481494e1c947d62db4a0
Source dataset
uspto-grants-1996_03
Patent number
US05496833

Reaction notes

Loading…