Benzoyl Peroxide → Methyl 4-(bromomethyl)benzoate

HRID 502507Notes

Reaction equation

HRID 502507 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:3][CH:2]=1.C1C(=O)N([Br:19])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:11][C:1]1[CH:2]=[CH:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 7455Methyl 4-methylbenzoateHCID 67184N-bromobutanimide

Product 1

HCID 256687Methyl 4-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 150 g of methyl p-toluate and 195.5 g of NBS in CCl4 (1.67 L) under N2 at 50° C. was added portion wise over 30 min, solid benzoyl peroxide (5.0 g). There was no exothermic reaction observed. After heating for 2 hours at 50° C., the yellow solution was heated at 65° C. for 6 hrs. There was still some unreacted starting material. The suspension was stirred overnight at 65° C. After cooling to room temperature (r.t), the precipitate formed was filtered off and washed with 150 mL of CCl4 and the filtrate was concentrated to afford a yellow oil that solidified on standing. The title compound, containing a small fraction of starting material was used in the next step without further purification.

Workup

  1. additionwas added portion wise over 30 min
  2. customno exothermic reaction
  3. temperaturethe yellow solution was heated at 65° C. for 6 hrs
  4. temperatureAfter cooling to room temperature (r.t)
  5. customthe precipitate formed
  6. filtrationwas filtered off
  7. washwashed with 150 mL of CCl4
  8. concentrationthe filtrate was concentrated
  9. customto afford a yellow oil that solidified

Sources & evidence

ORD record
ord-786e1531d25b4adba8bb555e523fc598
Source dataset
uspto-grants-2010_08
Patent number
US07776854B2

Reaction notes

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