Azobisisobutyronitrile → HCID 68546115, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 1-tert-butyl-3-iodo-5-methyl-benzene (1 g, 3.6 mmol, prepared according to Chem. Soc. Perkin Trans. I, 1987, page 859-866) in carbon tetrachloride (20 mL) under nitrogen. Add NBS (0.71 g, 1.1 equiv.) followed by AIBN (0.06 g, 0.1 equiv.) and heat overnight at 70° C. Filter in the morning, washing with hexanes. Concentrate filtrate and use crude. Dissolve this residue in THF (10 mL) under nitrogen and cool to 0° C. Add morpholine (0.64 mL, 2 equiv.) dropwise via syringe and stir 5 minutes with cooling. Remove ice bath and let warm to room temperature. After one hour concentrate to dryness and purify the residue on silica gel (Hexanes→4:1 Hexanes Ethyl Acetate) to give product (0.785 g, 60% over 2 steps). MS (ES), m/z 360.1 (M+1).

Provenance & Evidence