Reaction #2320148

Reaction equation

1,2-Dichloro-3-iodobenzene

benzylacetylene

→

title compound

1,2-dichloro-3-(3-phenylprop-1-ynyl)benzene

Solvents

triethylamine

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureat reflux for 2 hours
3. 3
   Otherwas partitioned between saturated sodium chloride and diethylether
4. 4
   DryingThe organic phase was dried with sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationthe filtrate was concentrated under reduced pressure
7. 7
   OtherThe residue was purified on silica gel (eluting with hexane)

Procedure

1,2-Dichloro-3-iodobenzene (4.39 g, 16.1 mmol), benzylacetylene (1.96 g, 16.9 mmol), copper(I) iodide (26 mg, 0.14 mmol) and bistriphenylphosphinepalladium(II)chloride (113 mg, 0.16 mmol) were combined in triethylamine (100 mL) and heated at reflux for 2 hours. The reaction was allowed to cool to room temperature and then was partitioned between saturated sodium chloride and diethylether. The organic phase was dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified on silica gel (eluting with hexane) to provide the title compound. MS (DCI/NH3) m/z 278 (M+NH4)+; 1H NMR (CDCl3) δ 3.90 (s, 2H), 7.13 (t, 1H), 7.2-7.5 (m, 7H).

Source