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

Participants

Reaction Steps

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--)].

Provenance & Evidence