反応 #2358600

反応方程式

HCl

ethyl 2-chloro-2-phenylacetate

1-fluoro-2-nitrobenzene

→

product

収率 44.9%

Ethyl 2-(3-fluoro-4-nitrophenyl)-2-phenylacetate

収率 44.9%

溶媒

water

DMF

反応条件

後処理

1. 1
   workup.ADDITIONwas carefully added dropwise
2. 2
   workup.ADDITIONThe reaction mix
3. 3
   抽出extracted with EE (3×50 ml)
4. 4
   洗浄the organic phases were washed with water and sat. aq. NaCl sol.
5. 5
   乾燥dried over MgSO4
6. 6
   濃縮concentrated under vacuum
7. 7
   その他The residue obtained
8. 8
   その他was purified by column chromatography (silica gel: mesh 100-200, eluent: 10% EE in cyclohexane)

実験手順

9.8 g of potassium tert. butylate were dissolved in 90 ml of DMF and cooled to −45° C. For this purpose, a mix of ethyl 2-chloro-2-phenylacetate (43.8 mmol, 8.7 g) and 1-fluoro-2-nitrobenzene (43.8 mmol, 4.6 ml) was carefully added dropwise and the mixture was stirred for a further 20 minutes. The reaction mix was set to pH 4 using 16% HCl, diluted with 25 ml of water and extracted with EE (3×50 ml). Once combined, the organic phases were washed with water and sat. aq. NaCl sol., dried over MgSO4 and concentrated under vacuum. The residue obtained was purified by column chromatography (silica gel: mesh 100-200, eluent: 10% EE in cyclohexane) and produced 5.9 g (44.9%) of product.

出典