反応 #46461

反応方程式

ammonium hydroxide

iodine

3-Benzyl-7-bromo-5-methyl-benzofuran-2-carbaldehyde

ammonium hydroxide

Iodine

→

3-benzyl-7-bromo-5-methyl-benzofuran-2-carbonitrile

収率 97.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture stirred for 30 minutes
2. 2
   その他The reaction mixture was quenched by addition of aqueous 10% sodium thiosulfate (20 ml) and brine (20 ml)
3. 3
   抽出The mixture was extracted with diethy ether
4. 4
   乾燥the combined organic phase was dried over magnesium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated under reduced pressure

実験手順

3-Benzyl-7-bromo-5-methyl-benzofuran-2-carbaldehyde (2.61 gm, 7.93 mmol) was added to a mixture of THF (10 ml) and concentrated ammonium hydroxide (80 ml). Iodine (2.2 g, 8.67 mmol) was added and the grey slurry was stirred overnight. Additional THF (20 ml), ammonium hydroxide (20 ml), and iodine (0.2 g, 0.8 mmol) were added, and the mixture stirred for 30 minutes. The reaction mixture was quenched by addition of aqueous 10% sodium thiosulfate (20 ml) and brine (20 ml). The mixture was extracted with diethy ether, and the combined organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 3-benzyl-7-bromo-5-methyl-benzofuran-2-carbonitrile (2.5 g, 97% yield). (M+H)+ 327.

出典