1-(2-chloroethyl)-4-fluorobenzene synthesis

Yield:41037-51-8 68%

Reaction Conditions:

with Carbon tetrachloride;triphenylphosphine at 90; for 1 h;Inert atmosphere;

Steps:

1-(2-Chloroethyl)-3-fluorobenzene (28).

To a stirred solution of triphenylphosphine (1.70 g, 6.5 mmol 1.3 equiv) in carbon tetrachloride(5.0 mL) at rt was added 2-(3-fluorophenyl)ethanol (620 μL, 5.0 mmol 1.0 equiv) under an argon atmosphere. The resulting mixture was allowed to warm to 90 °C and stirred for additional 1 h.The resulting mixture was filtered through a pad of Celite and the filtrate was concentrated under reduced pressure to give the chloride 28 (538 mg, 3.39 mmol, 68% yield) as a yellow oil. 1H NMR(400 MHz, chloroform-d) δ 7.30-7.24 (m, 1H), 7.00-6.91 (m, 3H), 3.70 (t, J = 7.1 Hz, 2H), 3.05(t, J = 7.3 Hz, 2H); 19F NMR (376 MHz, chloroform-d) δ -113.1 (m, 1F); 13C NMR (101 MHz,chloroform-d) δ 162.9 (d, JC-F = 246.6 Hz), 140.5 (m), 130.0 (d, JC-F = 8.7 Hz), 124.5 (d, JC-F =1.9 Hz), 115.8 (d, JC-F = 21.2 Hz), 113.8 (d, J = 20.2 Hz), 44.5, 38.7; HRMS (EI) m/z calcd forC8H8ClF [M]+ 158.0299 found 158.0290.

References:

Shinya, Susumu;Kawai, Kentaro;Kobayashi, Naoki;Karuo, Yukiko;Tarui, Atsushi;Sato, Kazuyuki;Otsuka, Masato;Omote, Masaaki [Bioorganic and Medicinal Chemistry,2022,vol. 74,art. no. 117042] Location in patent:supporting information