Benzoyl Peroxide → HCID 19046452, compound

HRID 1781960Notes

Reaction equation

HRID 1781960 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 filtrate was concentrated in vacuo. The residue was purified by chromatography on silica using hexane as eluent to afford 3-t-butyl-5-chlorobenzyl bromide 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 6 h
  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-dac80fb0f36f4b17b2c012191b64c977
Source dataset
uspto-grants-1997_05
Patent number
US05633281

Reaction notes

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