Benzene, 1-fluoro-4-(2-isothiocyanatoethyl)- synthesis

Yield:2740-86-5 70%

Reaction Conditions:

with triethylamine in N,N-dimethyl-formamide at 50;

Steps:

4.1.4 General procedure for synthesis of isothiocyanates (44a-j)

General procedure: 1, 1-thiocarbonyldiimidazole 82 (1.2 equiv) was dissolved in dry DMF at 50°C. To this mixture, a solution of the appropriate amines 81a-j (1 equiv) and dry Et₃N (1 equiv) in dry DMF was slowly added dropwise. The mixture was stirred at 50°C, and the progress monitored by TLC or UPLC/MS. Then the reaction was cooled down, water was added, and the aqueous phase was extracted with EtOAc (3×10mL). Organic phases were washed with water and brine, dried over Na₂SO₄, filtered, and concentrated in vacuo. Purification by flash column chromatography was performed.

References:

Roberti, Marinella;Schipani, Fabrizio;Bagnolini, Greta;Milano, Domenico;Giacomini, Elisa;Falchi, Federico;Balboni, Andrea;Manerba, Marcella;Farabegoli, Fulvia;De Franco, Francesca;Robertson, Janet;Minucci, Saverio;Pallavicini, Isabella;Di Stefano, Giuseppina;Girotto, Stefania;Pellicciari, Roberto;Cavalli, Andrea [European Journal of Medicinal Chemistry,2019,vol. 165,p. 80 - 92]