Réaction #87617

Équation de réaction

ethyl 3-(aminomethyl)-6-chloro-2-fluorobenzoate

pivaloyl chloride

→

product

Rendement 63.3%

ethyl 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoate

Rendement 63.3%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreExcess of solvent was removed under vacuum
2. 2
   workup.ADDITIONthe residue was diluted with water
3. 3
   Extractionextracted with EtOAC
4. 4
   Concentrationconcentrated

Mode opératoire

To a solution of ethyl 3-(aminomethyl)-6-chloro-2-fluorobenzoate (0.540 g, 2.5 mmol) in THF (5 mL) was added pivaloyl chloride (0.335 g, 2.79 mmol) and TEA (0.1 mL) and the reaction mixture was stirred for 2-3 h at RT. Excess of solvent was removed under vacuum and the residue was diluted with water, extracted with EtOAC and concentrated to afford 0.500 g of the product. 1H NMR (300 MHz, DMSO d6): δ 1.11 (s, 9H), 1.31 (t, J=7.5 Hz, 3H), 4.26 (d, J=5.1 Hz, 2H), 4.39 (q, J=6.6 Hz, 2H), 7.33-7.43 (m, 2H), 8.13 (m, 1H).

Source