Benzoyl Peroxide → 3-(bromomethyl)phenyl benzoate

HRID 1975823Notes

Reaction equation

HRID 1975823 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:35]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][Br:35])[CH:11]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 69193Benzoic acid, 3-methylphenyl ester

Product 1

HCID 20521313-(bromomethyl)phenyl benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 20.83 g (0.098 mol) of 3-methylphenyl benzoate in 280 mL of carbon tetrachloride was added a catalytic amount of benzoyl peroxide, followed by 20.96 g (0.118 mol) of N-bromosuccinimide. The reaction mixture was stirred and heated under reflux overnight. After cooling to room temperature, the solid material was filtered off. The filtrate was washed with 100 mL of water. The organic phase was removed and dried over magnesium sulfate, filtered and evaporated to dryness in a rotary evaporator. The crude product (31.3 g) was purified by HPLC to give 20.61 g and was used directly in the next step.

Workup

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. filtrationthe solid material was filtered off
  4. washThe filtrate was washed with 100 mL of water
  5. customThe organic phase was removed
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness in a rotary evaporator
  9. customThe crude product (31.3 g) was purified by HPLC
  10. customto give 20.61 g

Sources & evidence

ORD record
ord-b4a0f8e61af649c98d755cfcb2ccc74f
Source dataset
uspto-grants-1994_02
Patent number
US05288871

Reaction notes

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