Reference of 61881-19-4,Some common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To the stirred suspension of p-methoxybenzyl alcohol (2.00 g, 14.5 mmol)and N-phenyl-2,2,2-trifluoroacetimidate chloride (3.40 g, 16.3 mmol) inDCM (70 mL), NaH (60% in mineral oil, 0.635 g, 15.8 mmol) was added portionwise at 0C.The mixture was stirred for 2h at rt. After an addition of ice, the organic phase was washedwith water (3 x 40 mL), dried (MgSO4), filtered, and evaporated. The resulting residue wascrystallized from Et2O/PE, to give 1 as white needles (4.00 g, 89%). mp 90-91C, 1H NMR(360 MHz in CDCl3, ppm): delta 7.37 (2H, br d, J = 8.5 Hz, Ph), 7.29 (2H, br t, J = 2.0 Hz, J =6.5 Hz, J = 7.5 Hz, Ph), 7.08 (1H, br t, J = 1.0 Hz, J = 7.0 Hz, J = 7.5 Hz, Ph), 6.92 (2H, br d,J = 8.5 Hz, Ph-OCH3, PMB), 6.82 (2H, br d, J = 8.5 Hz, Ph-OCH3, PMB), 5.25 (2H, s, CH2,PMB), 3.83 (3H, s, OCH3, PMB), 13C NMR (90 MHz in CDCl3, ppm): delta 160.08 (Cquat-OCH3,PMB), 145.28 (q, JC-C-F = 35,0 Hz), 144.58 (Cquat arom), 130.42, 128.89, 127.23, 124.04,119.73 (CH arom), 116.38 (q, JC-F = 285,5 Hz), 114.13 (Cm PMB), 69.69 (CH2,PMB), 53.32 (OCH3, PMB), HRMS (ESI) m/z [M+Na] 332.0869; found 332.0859, AnalCalcd C16H14F3NO2 : Calcd. C 62.13, H 4.56, N 4.53; found C 62.30, H 4.59, N 4.44.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, its application will become more common.
Reference:
Article; Barroca-Aubry, Nadine; Benchekroun, Mohamed; Gomes, Filipe; Bonnaffe, David; Tetrahedron Letters; vol. 54; 37; (2013); p. 5118 – 5121;,
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