反応 #87567

反応方程式

1-chloro-2-nitrobenzene

N-hydroxy methyl trifluoro acetamide

→

desired product

N-(4-chloro-3-nitrobenzyl)-2,2,2-trifluoroacetamide

溶媒

sulphuric acid

反応条件

後処理

1. 1
   その他The reaction mass was quenched in ice cold water
2. 2
   抽出extracted with DCM
3. 3
   濃縮The organic layer was concentrated
4. 4
   その他the obtained crude product
5. 5
   その他was purified by column chromatography on silica gel eluting with 4% EtOAc

実験手順

To a solution of 1-chloro-2-nitrobenzene (10.0 g, 0.063 mmol) in conc. sulphuric acid (150 mL) was added N-hydroxy methyl trifluoro acetamide (9.98 g, 0.069 mmol). The reaction mixture was heated at 70-80° C. for 24 h. The reaction mass was quenched in ice cold water, neutralised with sodium hydroxide and extracted with DCM. The organic layer was concentrated and the obtained crude product was purified by column chromatography on silica gel eluting with 4% EtOAc: pet. ether to afford 5.5 g of desired product. 1H NMR (300 MHz, DMSO d6): 4.48 (d, J=3.9 Hz, 2H), 7.62-7.64 (m, 1H), 7.72-7.78 (m, 1H), 7.97-8.01 (m, 1H), 10.09 (brs, 1H).

出典