Benzoyl Peroxide → HCID 19046452, compound

HRID 1757237Notes

Reaction equation

HRID 1757237 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 6h. The mixture was cooled, filtered through celite and the filtrate 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) δ1.31 (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 6h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by chromatography on silica

Sources & evidence

ORD record
ord-5f701094615f4043b45cecee0d25df06
Source dataset
uspto-grants-1995_08
Patent number
US05444074

Reaction notes

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