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

참여 물질

반응 단계

13.44 G. (0.56 mole) of magnesium turnings were placed in a dried flask under N2 with 125 ml. of ether and a crystal of iodine. 6 Ml. of 65 ml. solution of 24.2 g. (0.14 mole) of p-methylthiobenzyl chloride in ether was added. After 3 to 5 minutes of stirring, the iodine color disappeared and the reaction began. After aging for 5 minutes, the rest of the benzyl chloride was added dropwise over 45 minutes. It was rinsed in with 10 ml. of ether and the reaction aged for 2 hours with stirring. 21 G. (0.128 mole) of 5-fluoro-2-methyl-1-indanone dissolved in 50 ml. of ether was added dropwise over 30 minutes. After aging for 1 hour, the milky supernatent mixture was decanted from the magnesium into 100 ml. of acetic acid. The flask and residual magnesium were rinsed into the acid solution with 4 × 50 ml. of benzene. 200 Ml. of water were added, the layers were separated and the organic layer was washed with 5 × 200 ml. water. It was 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.

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