Reaction #44787

Reaction equation

2-[4-[[4-(2-chloroethoxy)phenyl]methyl]phenyl]oxazole

sodium iodide

→

2-[4-[[4-(2-iodoethoxy)phenyl]methyl]phenyl]oxazole

Yield 78.5%

Solvents

2-butanone

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   TemperatureThe reaction was heated
3. 3
   Temperatureat reflux for 2 days
4. 4
   ConcentrationThe reaction was concentrated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
6. 6
   Washwashed with water
7. 7
   OtherThe combined organic layers were dried
8. 8
   Concentrationconcentrated
9. 9
   OtherThe residue was recrystallized from methanol

Procedure

A solution of 2-[4-[[4-(2-chloroethoxy)phenyl]methyl]phenyl]oxazole (1.7 g, 4.4 mmol) in 2-butanone (18 mL) was stirred as sodium iodide (7 g, 44 mmol) was added. The reaction was heated at reflux for 2 days. The reaction was concentrated. The residue was dissolved in ethyl acetate and washed with water. The combined organic layers were dried and concentrated. The residue was recrystallized from methanol to give 1.4 g of 2-[4-[[4-(2-iodoethoxy)phenyl]methyl]phenyl]oxazole, 1H NMR (400 MHz, CDCl3) δ 7.97 (d, 2H), 7.68 (s, 1H), 7.27 (d, 2H), 7.21 (s, 1H), 7.13 (d, 2H), 6.82 (d, 2H), 4.22 (t, 2H), 3.96 (s, 2H), 3.39 (t, 2H).

Source