Réaction #6323

Équation de réaction

NaHCO3

3-hydroxymethyl-2-iodoquinoline

triphenylphosphine

N-chlorosuccinimide

→

3-chloromethyl-2-iodoquinoline

Rendement 84.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Extractionthe mixture was extracted with ethyl acetate (20 mL)
2. 2
   LavageThe combined organic extracts were washed successively with 20-mL portions of dilute NaHCO3, water and brine
3. 3
   Séchagewere dried over MgSO4
4. 4
   ConcentrationConcentration and purification of the residue by radial PLC (silica gel, 10% ethyl acetate/hexanes)

Mode opératoire

To a stirred mixture of 3-hydroxymethyl-2-iodoquinoline prepared in accordance with Example 10 above (350 mg, 1.23 mmol) and triphenylphosphine (483 mg, 1.84 mmol) in 10 mL of dry DMF at -23° C. was added N-chlorosuccinimide (246 mg, 1.84 mmol), and the mixture was stirred for 1 h at -23° C. After the addition of 40 mL of dilute aqueous NaHCO3, the mixture was extracted with ethyl acetate (20 mL) and then ether (2×15 mL). The combined organic extracts were washed successively with 20-mL portions of dilute NaHCO3, water and brine, and were dried over MgSO4. Concentration and purification of the residue by radial PLC (silica gel, 10% ethyl acetate/hexanes) afforded 312 mg (84%) of 3-chloromethyl-2-iodoquinoline as a white crystalline solid: mp 138°-140° C. Recrystallization from hexanes afforded an analytical sample as colorless needles: mp 139°-140° C. 1H NMR (300 MHz, CDC13)δ8.17 (s, IH), 8.07 (d, 1H, J =9 Hz), 7.84 (d, 1H, J =9 Hz), 7.75 (t, 1H, J =9 Hz), 7.62 (t, 1H, J =9 Hz), 4.80 (s, 1H); IR (nujol) 1585, 1555, 1260, 1010, 780, 755, 710 cm-1.

Source