Compound 88
methyl 2-(5-(azetidin-1-yl)-2,4-dichlorophenoxy)propanoate
From: Practical and regioselective amination of arenes using alkyl amines
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Compound data: NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Following GP2 outlined for compound 45, in 1,1,1,3,3,3-hexafluoro-i-propanol (HFIP) but using 1.0 equiv. of dichloroprop methyl ester, 1.5 equiv. of azeditine hydrochloride, 1.5 equiv. of DIPEA and 6 equiv. of HClO4, dichloroprop methyl ester (25 mg, 0.1 mmol) gave 88 (8 mg, 24%) and 88* (3 mg, 10%) as white solids. Rf 0.38 [petrol–EtOAc (6:1)]; FT-IR νmax (film)/cm–1 2996, 2865, 1757, 1589, 1494, 1475, 1404, 1370, 13010, 1222, 1094; 1H NMR (400 MHz, CDCl3) δ 7.18 (1H, s), 6.02 (1H, s), 4.70 (1H, q, J = 6.8 Hz), 4.00 (4H, t, J = 7.3 Hz), 3.76 (3H, s), 2.28 (2H, quint, J = 7.3 Hz), 1.65 (3H, d, J = 6.8 Hz); 13C NMR (101 MHz, CDCl3) δ 172.2, 152.5, 147.4, 131.4, 113.3, 113.1, 102.2, 74.7, 54.1, 52.4, 18.5, 16.9; HRMS (APCI): Found M+ 303.0428, C13H15NO3Cl2 requires 303.0424.
