Methyl iodide → 9-Methylfluorene

HRID 2259277Notes

Reaction equation

HRID 2259277 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Li][CH2:15]CCC.IC>C1COCC1>[CH3:15][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 6853FluoreneHCID 178418339Butyllithium

Product 1

HCID 172999-MethylfluoreneYield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of fluorene (10.0 g, 60.0 mmol) in 100 mL of THF was added n-BuLi (66.6 mmol) at -78° C. This solution was then added to a chilled solution of iodomethane (15.04 g, 90.6 mmol) in 60 mL of THF. The temperature was kept at about -20° C. to maintain a clear solution. The mixture was allowed to warm to room temperature and then quenched with saturated aqueous NH4Cl and evaporated to a residue which was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried with MgSO4, filtered and evaporated to a solid. This solid was dissolved with hot pentane, stirred with decolorizing charcoal, filtered through a celite pad, and evaporated to get 10.0 g(92%) of 9-methyl fluorene was a white solid, mp 42°-43° C. FT-IR (KBr): 3065, 3039, 3016, 2962, 2926, 2864, 1478, 1445, 1309, 1023, 792 cm-1. NMR (300 MHz, CHCl3) δ 1.60-1.62(d, 3H, J=7.5 Hz), 3.93-3.97 (q, 1H, J=7.5 Hz), 7.32-7.38 (m, 4H) , 7.35-7.36 (d, 2H, J=8.0 Hz), 7.81-7.83(d, 2H, J=8.0 Hz).

Workup

  1. customwas kept at about -20° C.
  2. temperatureto maintain a clear solution
  3. customquenched with saturated aqueous NH4Cl
  4. customevaporated to a residue which
  5. customwas partitioned between ethyl acetate and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. customevaporated to a solid
  10. dissolutionThis solid was dissolved with hot pentane
  11. filtrationfiltered through a celite pad
  12. customevaporated

Sources & evidence

ORD record
ord-f0b1d8ae306440e78a417d9b208542e6
Source dataset
uspto-grants-1995_12
Patent number
US05472973

Reaction notes

Loading…