Reaktion #1923240

Reaktionsgleichung

Methyl 3-Iodo-4-hydroxybenzoate

4-Methoxyphenylacetylene

HCl

→

142

Ausbeute 71.0%

2-(4-Methoxy-phenyl)-benzofuran-5-carboxylic acid methyl ester

Ausbeute 71.0%

Lösungsmittel

DMF Piperidine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was cooled
2. 2
   ExtraktionThe aqueous layer was extracted with EtOAc
3. 3
   Sonstigeseparated
4. 4
   Sonstigedried
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto give a solid
7. 7
   SonstigeThe solid was triturated with MeOH
8. 8
   Filtrationfiltered

Vorschrift

A mixture of Methyl 3-Iodo-4-hydroxybenzoate (0.7 g, 2.5 mmol), 4-Methoxyphenylacetylene (0.33 g, 2.5 mmol), Pd(Cl)2(PPh3)2 (0.05 g) and CuI (0.03 g) in DMF/Piperidine (20 ml) was heated at 60° C. After 2 hr, the reaction was cooled and poured into 2N HCl. The aqueous layer was extracted with EtOAc and then separated, dried, concentrated to give a solid. The solid was triturated with MeOH, filtered to give 142 (0.5 g, 71%): Mp=157-159° C.; 1H NMR (CDCl3) δ 8.28 (d, 1 H, J=1.3 Hz), 7.97 (dd, 1 H, J=8.5 Hz, 1.7 Hz), 7.82-7.79 (m, 2 H), 7.51 (d, 1 H, 8.5 Hz), 6.99 (d, 2 H, J=8.3 Hz), 6.93 (d, 1 H, J=0.9 Hz), 3.94 (s, 3 H), 3.87 (s, 3 H); MS 283 (M+H)+

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