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

HRID 894175Notes

Reaction equation

HRID 894175 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 15 gm. (0.0655 mole) of methyl 5-bromo-o-toluate prepared according to Example 2 Step B in 75 ml. of carbon tetrachloride portionwise during 30 minutes with a mixture of 12.24 gm. (0.0688 mole) of N-bromosuccinimide and 130 mg. of benzoyl peroxide. Heat the resulting mixture at 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 8.92 gm. (0.655 mole) of 3-isopropylphenol, 75 ml. of dimethylformamide, 27.16 gm. (0.1965 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 to obtain the title product as an orange-red residual oil [yield 23.7 gm., pmr (CDCl3) 1.23 (6H,d, (CH3)2CH--), 2.85(1H,m, (CH3)2CH--), 3.90(3H,s,CH3O--), 5.40 (2H,s,CH2O--)].

Workup

  1. additionTreat a solution of 15 gm
  2. temperatureHeat the resulting mixture
  3. temperatureat reflux for 3 hours
  4. customseparate the succinimide
  5. filtrationby filtration
  6. customRemove the solvent under vacuum

Sources & evidence

ORD record
ord-741bae760a4e4852b805f4a484b68bc0
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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