反応 #80930

反応方程式

water

4-fluoro-2-nitro-6-methylaniline

iodine

tert-butyl nitrite

→

4-fluoro-2-nitro-6-methylphenyl iodide

収率 46.5%

溶媒

acetonitrile

acetonitrile

反応条件

後処理

1. 1
   workup.ADDITIONUpon completion of addition
2. 2
   workup.STIRRINGthe reaction mixture was stirred at ambient temperature for about 16 hours
3. 3
   その他Excess iodine was destroyed
4. 4
   抽出The mixture was then extracted with two 250 mL portions of diethyl ether
5. 5
   乾燥The combined extracts were dried with magnesium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮The filtrate was concentrated under reduced pressure to a residue
8. 8
   洗浄Elution
9. 9
   濃縮concentrated under reduced pressure

実験手順

A mixture of 4.4 grams (0.026 mole) of 4-fluoro-2-nitro-6-methylaniline, 13.2 grams (0.052 mole) of iodine, and 5.5 grams (0.029 mole) of copper(I) iodide in 125 mL of acetonitrile was stirred, and a solution of 4.6 mL (0.039 mole) of tert-butyl nitrite in 25 mL of acetonitrile was added dropwise during a 10 minute period. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 16 hours. After this time the reaction mixture was poured into 300 mL of water. Excess iodine was destroyed using sodium meta-bisulfite. The mixture was then extracted with two 250 mL portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using 1:3 methylene chloride: petroleum ether. The product-containing fractions were combined and concentrated under reduced pressure, yielding 3.4 grams of 4-fluoro-2-nitro-6-methylphenyl iodide. The NMR spectrum was consistent with the proposed structure. The reaction was repeated to obtain more product.

出典