Reacción #87545

Ecuación de reacción

2-chlorobenzoic acid

2,2,2-trifluoro-N-(hydroxymethyl)acetamide

→

title product

Rendimiento 81.4%

2-chloro-5-{[(trifluoroacetyl)amino]methyl}benzoic acid

Rendimiento 81.4%

Disolventes

H2SO4

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred for 2 h
2. 2
   OtroThe precipitate obtained
3. 3
   Filtraciónwas collected by filtration
4. 4
   Otrodried
5. 5
   Otrore-crystallized from toluene/butan-2-one (7:1)

Procedimiento

To a solution of 2-chlorobenzoic acid (0.500 g, 3.49 mmol) in conc. H2SO4 was added 2,2,2-trifluoro-N-(hydroxymethyl)acetamide (0.547 g, 3.49 mmol). The mixture was stirred at RT for 16 h. The reaction mixture was poured into ice-water and stirred for 2 h. The precipitate obtained was collected by filtration, dried and re-crystallized from toluene/butan-2-one (7:1) to afford 0.800 g of the title product. 1H NMR (300 MHz, DMSO d6): δ 4.42 (d, J=6.0 Hz, 2H), 7.43 (d, J=9.9 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.71 (s, 1H), 10.06 (br s, 1H), 13.47 (br s, 1H); MS (m/z): 280.18 (M−H)−.

Fuente