Iodine → 5-Fluoro-2-methyl-1-(p-methylthiobenzyl)-indene

Participants

Reaction Steps

13.44 Grams (0.56 mole) of magnesium turnings are placed in a dried flask under N2 with 125 ml. of ether and a crystal of iodine. Six ml. of 65 ml. solution of 24.2 g. (0.14 mole) of p-methylthiobenzyl chloride in ether is added. After 3 to 5 minutes of stirring the iodine color disappears and the reaction begins. After aging for 5 minutes, the rest of the benzyl chloride is added dropwise over 45 minutes. It is rinsed in with 10 ml. of ether and the reaction aged for 2 hours with stirring. 21 Grams (0.128 mole) of 5-fluoro-2-methyl-1-indanone dissolved in 50 ml. of ether is added dropwise over 30 minutes. After aging for 1 hour, the milky supernatent mixture is decanted from the magnesium into 100 ml. of acetic acid. The flask and residual magnesium are rinsed into the acid solution with 4 × 50 ml. of benzene. Two hundred ml. of water are added, the layers are separated and the organic layer is washed with 5 × 200 ml. water. It is stripped to dryness after drying over Na2SO4. The crude reaction product is crystallized from hexane to give pure 5-fluoro-2-methyl-1-(p-methylthiobenzyl)-indene, melting point 58°-59°C.

Provenance & Evidence