Réaction #87567

Équation de réaction

1-chloro-2-nitrobenzene

N-hydroxy methyl trifluoro acetamide

→

desired product

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

Solvants

sulphuric acid

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mass was quenched in ice cold water
2. 2
   Extractionextracted with DCM
3. 3
   ConcentrationThe organic layer was concentrated
4. 4
   Autrethe obtained crude product
5. 5
   Autrewas purified by column chromatography on silica gel eluting with 4% EtOAc

Mode opératoire

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).

Source