Iodobenzene → HCID 379768, compound

HRID 1757689Notes

Reaction equation

HRID 1757689 reaction equation
[CH2:1]1[C:6](=O)N(I)[C:3](=[O:4])[CH2:2]1.CC1C=CC(S(O[I:20](O)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=O)=O)=CC=1.[CH3:28][CH:29]1CCC[CH:30]1O.I[C:36]1C=CC=CC=1>CO>[I:20][C:21](=[C:26]1[CH2:25][CH2:24][CH2:23][CH:22]1[CH3:36])[C:3]([C:2]1[CH:1]=[CH:6][CH:30]=[CH:29][CH:28]=1)=[O:4]

Participants

6

Reactant 4

HCID 11575IodobenzeneHCID 322052-MethylcyclopentanolHCID 120273N-IodosuccinimideHCID 325434[Hydroxy(tosyloxy)iodo]benzene

Product 1

HCID 379768HCID 379768, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NIS (220 mg, 0.98 mmol) and HTIB (39 mg, 0.98 mmol) were added in one portion to a stirring solution containing 2-methyl-1-cyclopentanol in 10 mL of methanol. The reaction mixture was protected from light and stirred at room temperature for 16 hours. The reaction was worked up as usual. After evaporation of solvent under vacuum a light green oily residue was obtained (323 mg). The GC/Ms spectrum of the crude residue showed that starting material was present along with iodobenzene and the product. The product was isolated by means of silica gel column chromatography (40-140 mesh). Iodobenzene was eluted first with hexanes. The product was eluted next with 1:1 mixture of CH2Cl12 /hexanes and after solvent evaporation under vacuum, a light green oil was obtained (86.2 mg, 28%). The oil was characterized by spectroscopy: 1H-NMR (CDCl3): (E-isomer) δ1.24 (d, 7.2 Hz, 3H), 2.20-2.96 (m, 7H), 7.47 (t, 7.2 Hz, 2H), 7.58 (t, 7.2 Hz, 1H) , 7.92 (d, 7.8 Hz, 2H); (Z-isomer); δ0.92 (d, 7.2 Hz, 3H), 2.20-2.96 (m, 7H), 7.47 (t, 7.2 Hz, 2H), 7.58(t, 1H), 7.96 (d, 8 Hz, 2H); 13C-NMR (CDCl3) (Z-isomer) δ21.23, 24.07, 38.0, 40.69, 42.06, 87.39, 129.91, 130.1, 131.2, 131.32, 134.79, 135.76, 163.22, 194.02; (E-isomer) δ19.62, 26.87, 34.09, 34.72, 45.95, 85.55, 130.05, 131.19, 134.79, 135.59, 162.29, 1.94.20; IR (neat) 1665 (s), 1590 (w), 1450 (m), 1350 (w), 1300 (m), 1245(s), 1175 (m), 1050 (m), 1015 (m), 975 (w), 690 (m) cm-1 ; MS m/z (rel. int.) 326 (M+, 5), 311 (M-Ch3, 5), 199 (M-I, 11), 157 (49), 129(25), 105 (C6H5CO, 55), 77 (C6H5, 100).

Workup

  1. customAfter evaporation of solvent under vacuum a light green oily residue
  2. customwas obtained (323 mg)
  3. customThe product was isolated by means of silica gel column chromatography (40-140 mesh)
  4. washIodobenzene was eluted first with hexanes
  5. washThe product was eluted next with 1:1 mixture of CH2Cl12 /hexanes
  6. customafter solvent evaporation under vacuum
  7. customa light green oil was obtained (86.2 mg, 28%)

Sources & evidence

ORD record
ord-5d70674f1c47451a97a430964ef1a5ad
Source dataset
uspto-grants-1995_08
Patent number
US05446203

Reaction notes

Loading…