Benzoyl Peroxide → Methyl 4-bromo-2-(bromomethyl)benzoate

HRID 894171Notes

Reaction equation

HRID 894171 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:8][C:6]1[C:5]([C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=[C:2]([Br:1])[CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 22031226Methyl 4-bromo-2-methylbenzoate

Product 1

HCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Treat a solution of 17.48 gm. (0.0763 mole) of methyl 5-bromo-o-toluate in 85 ml. of carbontetrachloride portionwise during 30 minutes with a mixture of 14.26 gm. (0.0801 mole) of N-bromosuccinimide and 152 mg. of benzoyl peroxide. Heat the resulting mixture under reflux for 3 hours. Cool to room temperature and separate the succinimide by filtration. Remove the solvent under vacuum to obtain methyl α,5-dibromo-o-toluate as a yellow residual oil. Heat a mixture of 7.18 gm. (0.0763 mole) of phenol, 85 ml. of dimethylformamide, 31.63 gm. (0.2289 mole) of potassium carbonate and the methyl α,5-dibromo-o-toluate obtained above at 55°-60° C. for 2 hours. Cool the mixture and pour into 350 ml. of water. Extract the resulting oil into ether, wash with water and dry over anhydrous magnesium sulfate. Remove the solvent under vacuum and allow the residual oil (24.51 gm.) to stand overnight. Separate the solids formed by placing the mixture on porous plates. Wash the solids with petroleum ether to obtain the title compound [yield 13.33 gm., m.p. 69.5°-70.5° C., pmr (CDCl3) 3.90(3H, s, CH3O--), 5.40(2H, s, CH2O--)].

Workup

  1. additionTreat a solution of 17.48 gm
  2. temperatureHeat the resulting mixture
  3. temperatureunder reflux for 3 hours
  4. customseparate the succinimide
  5. filtrationby filtration
  6. customRemove the solvent under vacuum

Sources & evidence

ORD record
ord-00841c461bb5480ba6657e8de27e1f92
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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