Benzoyl Peroxide → Methyl 4-(bromomethyl)benzoate

HRID 2375312Notes

Reaction equation

HRID 2375312 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). No exothermic reaction was observed. After heating for 2 hours at 50° C., the yellow solution was heated up at 65° C. for 1 d. After cooling down to rt, 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 up at 65° C. for 1 d
  4. temperatureAfter cooling down to rt
  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-8eb6a85af7ec4797a9e38ca1ccb0ca80
Source dataset
uspto-grants-2008_12
Patent number
US07465736B2

Reaction notes

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