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

HRID 1606709Notes

Reaction equation

HRID 1606709 reaction equation
[Mg].II.[CH3:4][S:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10]Cl)=[CH:8][CH:7]=1.C(Cl)C1C=CC=CC=1.[F:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[C:28](=O)[CH:27]([CH3:33])[CH2:26]2>CCOCC>[F:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH:28]([CH2:10][C:9]1[CH:12]=[CH:13][C:6]([S:5][CH3:4])=[CH:7][CH:8]=1)[C:27]([CH3:33])=[CH:26]2

Participants

7

Reactant 5

HCID 807Iodine2×HCID 7503Benzyl ChlorideHCID 701281-(Chloromethyl)-4-(methylthio)benzeneHCID 30162575-Fluoro-2-methylindan-1-oneHCID 5462224Magnesium

Product 1

HCID 215218885-Fluoro-2-methyl-1-(p-methylthiobenzyl)-indene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

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.

Workup

  1. waitAfter aging for 5 minutes
  2. washIt was rinsed in with 10 ml
  3. waitof ether and the reaction aged for 2 hours
  4. stirringwith stirring
  5. waitAfter aging for 1 hour
  6. customthe milky supernatent mixture was decanted from the magnesium into 100 ml
  7. washThe flask and residual magnesium were rinsed into the acid solution with 4 × 50 ml
  8. additionof water were added
  9. customthe layers were separated
  10. washthe organic layer was washed with 5 × 200 ml
  11. dry with materialafter drying over Na2SO4
  12. customThe crude reaction product
  13. customis crystallized from hexane

Sources & evidence

ORD record
ord-88cac19d4cd8460c85c5ca5c12669220
Source dataset
uspto-grants-1976_04
Patent number
US03953520

Reaction notes

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