反応 #553575

反応方程式

methyl 3-iodobenzoate

4-iodotoluene

→

methyl 4'-methylbiphenyl-3-carboxylate

収率 34.9%

反応条件

後処理

1. 1
   温度the temperature increased spontaneously to 240°
2. 2
   温度to cool to 210°
3. 3
   ろ過was filtered
4. 4
   濃縮the resulting filtrate was concentrated in vacuum
5. 5
   その他to provide the crude product
6. 6
   workup.DISTILLATIONColumn chromatography on silica gel (elution=50-100% benzene/hexane) followed by distillation

実験手順

To a stirred solution of 25.2 g of methyl 3-iodobenzoate and 21.0 g of 4-iodotoluene at 180°-190° under nitrogen was added 30.3 g of copper powder portionwise over 1 hour. When approximately one-third of the copper had been added, the reaction initiated and the temperature increased spontaneously to 240°. The mixture was allowed to cool to 210°, then was held at 210° during the addition of the remaining copper and for an additional hour. The mixture was allowed to cool to room temperature and was filtered employing benzene as solvent; the resulting filtrate was concentrated in vacuum to provide the crude product. Column chromatography on silica gel (elution=50-100% benzene/hexane) followed by distillation furnished 7.60 g of methyl 4'-methylbiphenyl-3-carboxylate [bp: 114°-115° C. (0.025 torr)] as a colorless oil; NMR (200 MHz, CDCl3): δ 8.27 (br S, 1H); 7.99 (d, 1H); 7.77 (d, 1H); 7.50 (t, 1H); 7.39 (A2B2, 4H); 3.94 (s, 3H); 2.41 (s, 3H).

出典