M-Xylene → HCID 12195664, compound

Participants

Reaction Conditions

Reaction Steps

A 500 mL, 3-neck rounded bottom flask equipped with a magnetic stirring bar and a reflux condenser, was filled with nitrogen atmosphere and charged with 71.16 g of AlCl3 (0.53 mol, 2.3 eq.) dissolved in 240 mL of chlorobenzene. At room temperature 28.38 mL of m-xylene (0.23 mol, 1 eq.) were added dropwise obtaining a light yellow suspension. The flask was then cooled to 0° C. and 28.68 mL of 2-bromoisobutyryl bromide (0.23 mol, 1 eq.) were slowly added. At the end of the addition a dark-red slurry was obtained. The reaction mixture was then allowed to warm up to r.t. and stirred for 2 hours. Then it was transferred into a flask containing a solution of ice/HCl 37%=3/1. The organic phase was extracted with Et2O (3×200 mL): the combined organic phases were dried over Na2SO4, filtered and the solvent was removed in vacuo. An orange oil was obtained as product (37.48 g, yield 93.5%). The latter was used as such without further purification in the next step.

Provenance & Evidence